Triethylamine → trans-N-[2-(Dimethylamino)cyclohexyl]alpha,alpha,alpha-trifluoro-p-toluamide

HRID 26251

반응식

HRID 26251 반응식
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[CH3:14][N:15]([CH3:23])[CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[NH2:22].C(N(CC)CC)C>>[CH3:14][N:15]([CH3:23])[C@@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[NH:22][C:7]([C:6]1[CH:10]=[CH:11][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=1)=[O:8]

참가 물질

4

반응물 3

HCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 12447266N1,N1-dimethylcyclohexane-1,2-diamine

생성물 1

HCID 53682390trans-N-[2-(Dimethylamino)cyclohexyl]alpha,alpha,alpha-trifluoro-p-toluamide

실험 절차

The titled amide was prepared according to general procedure B using p-trifluoromethyl-benzoyl chloride (4.17 g.; 0.02 mole), N,N-dimethylcyclohexane-1,2-diamine (2.84 g.; 0.02 mole) and triethylamine (2.02 g., 0.02 mole). The crude solid was crystallized from ether to give 4.766 g. (77% yield) of colorless needles, m.p. 141°-142°, raised to 141.5°-142.5° on recrystallization. uv λmax 222 nm (ε 11,450), sh 245 (5,550); sh 260 (3,400); sh 276 (1.750). ir NH 3310; =CH 3030; N-alkyl 2770, 2740; C=O 1635; C=O 1575, 1510; amide II 1550; CF3 /ether 1330, 1190, 1165, 1130, 1105, 1065, 1020; aromatic 860; nmr in CDCl3 at 100 MHz was in accord. Mass spectrum M+ 314.

후처리

  1. customThe crude solid was crystallized from ether
  2. customto give 4.766 g

출처 및 근거

ORD 기록
ord-6a868260414a4df599a3e4b8bdb3c653
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04148914

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