反応 #54534

ord-dcea2207afd142f6aabad091e6e134d9

反応方程式

CN(C)[C@@H]1CCCC[C@H]1N
trans-2-(dimethylamino)cyclohexylamine
O=C(Cl)c1cccc(C(F)(F)F)c1
3-trifluoromethylbenzoyl chloride
Cc1ccc(S(=O)(=O)O)cc1
p-toluenesulfonic acid
→
CN(C)[C@@H]1CCCC[C@H]1NC(=O)c1cccc(C(F)(F)F)c1.Cc1ccc(S(=O)(=O)O)cc1
amide
収率 47.0%
CN(C)[C@@H]1CCCC[C@H]1NC(=O)c1cccc(C(F)(F)F)c1.Cc1ccc(S(=O)(=O)O)cc1
trans-N-[2-(dimethylamino)cyclohexyl]-m-trifluoromethylbenzamide p-toluenesulfonate
収率 47.0%

反応物

CN(C)[C@@H]1CCCC[C@H]1N
trans-2-(dimethylamino)cyclohexylamine
O=C(Cl)c1cccc(C(F)(F)F)c1
3-trifluoromethylbenzoyl chloride
Cc1ccc(S(=O)(=O)O)cc1
p-toluenesulfonic acid

試薬

なし

溶媒

CCOCC
ether

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他was crystallized from MeOH-ether, 47% yield, colorless plates, m.p. 208°-209°

実験手順

This titled amide was prepared by general procedure B from trans-2-(dimethylamino)cyclohexylamine and 3-trifluoromethylbenzoyl chloride. The crude oil was converted to the salt with 1 mole of p-toluenesulfonic acid in ether, and was crystallized from MeOH-ether, 47% yield, colorless plates, m.p. 208°-209°. uv λmax 222 nm (ε 22,150); sh 227 (17,900); sh 259 (1,550); sh 266 (1,100); sh 274 (566). ir NH/N+H 3280, 3040; C=O 1660; C=C/amide II 1615, 1595, 1550, 1495; CF3 /SO3- /CN 1335, 1320, 1275, 1200, 1180, 1160, 1120, 1075, 1035, 1010; aromatic/SO3- 705, 690, 680. NMR in CDCl3 (100 MHz) was in accord. Mass spectrum M+ 314.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US04148914uspto-grants-1979_04