N,N'-(5,7-dimethyl adamantane-1,3-diyl) diacetamide synthesis
- Product Name:N,N'-(5,7-dimethyl adamantane-1,3-diyl) diacetamide
- CAS Number:14931-70-5
- Molecular formula:C16H26N2O2
- Molecular Weight:278.39
Yield:14931-70-5 92%
Reaction Conditions:
Stage #1: 1,3-dimethyladamantanewith nitric acid at 25; for 1 h;
Stage #2: acetonitrile for 0.5 h;
Stage #3: acetonitrilewith sulfuric acid at 20; for 4 h;Ritter Amidation;
Steps:
Compounds 2a-2g. General procedure
General procedure: To a fuming nitric acid (see the table) compound 1a-1g was added in portions with stirring at a temperature no higher than 25°C. The resulting solution was stirred for 1.5 hours at 25°C. Then acetonitrile was added dropwise to the reaction mixture, it was maintained for 1 hour, then conc. H2SO4 (96% for compounds 1a-1dand 98% for compounds 1e-1g) was added dropwise and the mixture was kept at room temperature for a preset time. The solution was poured onto 600 g of crushed ice and adjusted to pH 9 with NaHCO3 under stirring and cooling to prepare compounds 2a-2d or adjusted to pH 5 in the preparation of 2e-2g compounds. Then, the aqueous layer was decanted from the viscous oily reaction product, 30 mL of ethylacetate was added to the residue. The precipitate was filtered off, washed with water, and dried.
References:
Klimochkin, Yu. N.;Ivleva;Serzhantova;Shiryaev;Moiseev [Russian Journal of Organic Chemistry,2017,vol. 53,# 8,p. 1170 - 1175][Zh. Org. Khim.,2017,vol. 53,# 8,p. 1156 - 1161,6]
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