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10g <strong>[702-79-4]1,3-dimethyladamantane</strong>,36.8mL of acetonitrile is heated to 60 to 65 ,Slowly control the internal temperature not to drop 75mL concentrated sulfuric acid over 80 ,After the addition was completed, the reaction was carried out at 65 to 70 C for 10 h. The reaction mixture was quenched with ice water. After extraction with dichloromethane twice, the organic phases were combined, washed with organic phase, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure at 40 C The product has a yield of 73.5% and a purity of 99.7%.
With sulfuric acid; at 65 - 80℃; for 10h;Product distribution / selectivity;
Example-1: Preparation of l-acetamido-3,5-dimethyI adamantane :A mixture of 1,3 -dimethyl adamantane (10 grams) and acetonitrile (36.8 ml) was heated to 60-65C. Sulphuric acid (75 ml) was slowly added to the above reaction mixture at below 80C. The reaction mixture was stirred for 10 hours at 65-70C. The reaction mixture was quenched with ice water. The reaction mixture was extracted with methylene chloride. The organic and aqueous layers were separated. The aqueous layer was extracted with methylene chloride and the organic layer was washed with water. The organic layer was dried with sodium sulphate. The methylene chloride from the organic layer was distilled off under reduced pressure at below 40C to get the title compound. Yield: 12.5 grams.Purity by GC: 99.47%; Example-2: Preparation of l-acetamido-3,5-dimethyl adamantane : A mixture of <strong>[702-79-4]1,3-dimethyl adamantane</strong> (10 grams) and acetonitrile (36.8 ml) was heated to 60-65C. Sulphuric acid (75 ml) was slowly added to the above reaction mixture at below 8O0C. The reaction mixture was stirred for 10 hours at 65-70C. The reaction mixture was quenched with ice water. The reaction mixture was extracted with toluene. The organic and aqueous layers were separated. The aqueous layer was extracted with toluene and the organic layer was washed with water. The organic layer was dried with sodium sulphate. The toluene from the organic layer was distilled off under reduced pressure at below 700C to get the title compound. Yield: 12.3 grams
Bromide (500 gm) was added to dimethyladamantane (100 gm) under stirring for 1 hour 30 minutes at 25 to 30C. The reaction mass maintained for 12 hours at 25 to 30C and the reaction mass was poured in water and methylene chloride under stirring at 5 to 10C. To the reaction mass was added sodium sulfite (20%, 1000 ml) at 0 to 5C and stirred for 30 minutes at 0 to 5C. The layers were separated and the organic layer was distilled off completely under vacuum at below 45C to obtain a residue. The residue was dissolved in acetonitrile (600 ml). The solution was cooled to 0 to 5C and then added concentrated sulfuric acid (300 ml) drop wise for 2 hours at 0 to 5C. Then, the contents were maintained for 14 hours at 25 to 30C and the reaction mass was poured into a mixture of water and methylene chloride under stirring at 0 to 5C. The layers were separated and the organic layer was distilled off completely under vacuum at below 45C to obtain a residue. To the residue was added water (500 ml) at 35 to 40C and stirred for 30 minutes at 50C. The reaction mass was cooled to 25 to 30C and maintained for 2 hours at 25 to 30C, filtered. The solid obtained was dried at 45C for 6 hours to obtain 130 gm of l-acetamido-3, 5 -dimethyl adamantane.
12.8 g
With sulfuric acid; at 25 - 45℃;
Into <strong>[702-79-4]1,3-dimethyladamantane</strong> (10grams), sulphuric acid (56ml) added andslowly acetonitrile (37 .5rnl) was added at .25C-45C. The reaqtion mixturewas stirred at 25C-45C. The water was added in reaction mixture at 200C-300C. Then filtration followed by water washing to get ihe wet cake of titlecompound.Yield: 15.06grams wet cake (12.8grams on dried basis)Purity by GC: 99.50%Water content (moisture): 15%w jw
59.9 g
With sulfuric acid; In tert-butyl alcohol; at 60℃; for 20h;
<strong>[702-79-4]1,3-dimethyl adamantane</strong> 50g three-necked flask 1L, acetonitrile 254 mL, was charged with t- butanol 28.2 g, heating at 60 C., 895 g sulfuric acid It was slowly added dropwise over a period of 2 hours. It was heated 18 hours at 60 C. After the dropwise addition. The reaction was poured into ice-cold water, and extracted with dichloromethane 700 mL. The organic layer was washed with water, and recrystallized from hexane 300mL After concentration under reduced pressure to give 1-acetamido-3,5-dimethyl adamantane 59.9 g.
With sulfuric acid; In tert-butyl alcohol; at 50 - 70℃; for 18h;
40 g of <strong>[702-79-4]1,3-dimethyl adamantane</strong> and 235 ml of sulfuric acid to give a layer of colorless liquid, ice water cooled to below 30 degrees; Stir under the drop of 95g acetonitrile, exothermic, control the internal temperature of the system up to no more than 75 degrees;After the dropwise addition, the controlled temperature was allowed to react at 50-70 C for 18 h and cooled to room temperature. Pour into 350ml ice water, stir; Extraction (100 ml X3) with dichloromethane, the organic phases were combined, dried and concentrated to give 46-48 g of a white solid powder.
With tert-butyl alcohol;sulfuric acid; at 50 - 80℃; for 6h;
A mixture of <strong>[702-79-4]1,3-dimethyladamantane</strong>, acetonitrile and t-butanol heat to 50 to 80C and add conc. sulphuric acid slowly within 3 hours. Maintain at 70 - 80C for 3 hours. The reaction mixture product was poured in to ice and extracted with dichloromethane and wash the dichloromethane layer with water and sodium bicarbonate solution. Wash with water and dry with sodium sulphate. Distilled the dichloromethane and concentrated of organic layer and add n-Hexane and reflux. Cool to 0C and filter the compound and wash with chilled n-hexane and dry the compound 1-acetamido-3,5-dimethyl adamantane.
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