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CAS No. : | 1633-82-5 | MDL No. : | MFCD00007463 |
Formula : | C3H6Cl2O2S | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | GPKDGVXBXQTHRY-UHFFFAOYSA-N |
M.W : | 177.05 | Pubchem ID : | 15410 |
Synonyms : |
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Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P261-P280-P305+P351+P338-P310 | UN#: | 3265 |
Hazard Statements: | H314-H335 | Packing Group: | Ⅱ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With pyridine;dmap; In dichloromethane; for 40h; | To a solution of <strong>[23218-93-1]3-amino-5-nitro-benzoic acid methyl ester</strong> (45 g, 229 mmol, 1 equiv) in [CH2CI2] (450 ml) was added pyridine (18.5 [ML,] 229 mmol, [1] equiv), DMAP (100 mg, 0.8 [MMOL,] catalytic) and 3-chloropropanesulfonyl chloride (28 [ML,] 230 [MMOL).] The resulting mixture was stirred for [40] h then diluted with EtOAc. The organic phase was diluted with 2MN HCI. The resulting solid was filtered to give [3- (3-CHLORO-PROPANE-1-SULFONYLAMINO)-5-] nitro-benzoic acid methyl ester (23 g, 32%). The filtrate was separated and the organic phase was washed with saturated aqueous [NAHCO3] solution, dried over [MGS04] and concentrated in vacuo. The residue was triturated with EtOAc and iso-hexane to give a further 50 g (65%) of [3- (3-CHLORO-PROPANE-1-SULFONYLAMINO)-5-NITRO-BENZOIC] acid methyl ester, as a pale brown solid, which was used in the next step without further purification. LC/MS t = 3.11 min, [[MH]] = 335. |
65% | With pyridine; 4-(N,N-dimethylamino)phenol; In dichloromethane; for 40h; | To a solution of <strong>[23218-93-1]3-amino-5-nitro-benzoic acid methyl ester</strong> (D1) (45 g, 229 mmol, 1 equiv) in CH2CI2 (450 mi) was added pyridine (18.5 ML, 229 mmol, 1 equiv), DMAP (100 mg, 0.8 mmol, catalytic) and 3-chloropropanesulfonyl chloride (28 ML, 230 MMOL, 1 equiv). The resulting mixture was stirred for 40 h then diluted with AcOEt. The organic phase was diluted with 2N aqueous HCI solution. The resulting solid was filtered to give 3- (3-chloro-propane-1- sulfonylamino)-5-nitro-benzoic acid methyl ester (23 g, 32%). The filtrate was separated and the organic phase was washed with saturated aqueous NAHC03 solution, dried over MGS04 and concentrated in vacuo. The residue was triturated with AcOEt and iso-hexane to give a further 50 g (65%) of 3- (3-CHLORO-PROPANE-L-SULFONYLAMINO)-5-NITRO-BENZOIC acid methyl ester (D14) as a pale brown solid. [M-H]-= 334.9, RT = 3.11 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tetrahydrofuran; at 20℃; for 0.5h; | EXAMPLE 24 2-[4-((4S,5R)-4,5-Bis-(4-chloro-phenyl)-1-{4-[2-(11,1-dioxo-isothiazolidine-2-yl)-ethyl]-piperazine-1-carbonyl}-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl)-3-ethoxy-phenyl]-2-methyl-propionitrile To a stirred solution of 1-Boc-4-(2-aminoethyl)-piperazine (1.26 g, 6.8 mmol, Aldrich) and triethylamine (1 mL) in tetrahydrofuran (10 mL), 3-chloro-propylsulfonyl chloride (0.68 mL, 6.94 mmol, Aldrich) was added slowly at room temperature. The mixture was stirred for 30 min at room temperature and the reaction was quenched with water. It was extracted with ethyl acetate and the extracts were combined and dried over anhydrous sodium sulfate. The solids were filtered off, and the filtrate was concentrated in vacuo to give 4-[2-(3-chloro-propane-1-sulfonylamino)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | solution of <strong>[112734-22-2][(4-bromo-2-fluorophenyl)methyl]amine</strong> (2.Og, 9.8mmol) and triethylamine (2.73ml, 19.6mmol) in dimethylformamide (20ml) was treated with 3- chloropropanesulfonyl chloride (1.74g, 9.8mmole) dropwise over 10 minutes with stirring under argon. This mixture was stirred for 30 minutes before being treated with sodium hydride (60percent suspension in mineral oil, 1.176g, 29.4mmol) portionwise and the reaction mixture stirred at room temperature for 16 hours. The reaction mixture was partitioned between water and dichloromethane. The organic layer was dried over sodium sulphate and evaporated under reduced pressure. Sample was then purified by column chromatography on silica using 10 to 90percent ethyl acetate in n-pentane to afford the title compound as an oil (1.7g, 55percent).LC/MS (ES): Found 308 310 (ES+), retention time 2.73mins. Ci0H11 BrFNO2S requires 307 309.1H-NMR (400MHz, CDCI3): 2.34 (2H, m), 3.19 (4H, m), 4.20 (2H, d, J=I Hz), 7.22-7.35 (3H, m). |
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