2-Chloroethyl isocyanate → Ethyl 2-(2-oxoimidazolidin-1-yl)-4-(trifluoromethyl)thiazole-5-carboxylate

반응식

NC1SC(C(OCC)=O)=C(C)N=1.[NH2:13][C:14]1[S:15][C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:17]([C:19]([F:22])([F:21])[F:20])[N:18]=1.Cl[CH2:29][CH2:30][N:31]=[C:32]=[O:33]>>[O:33]=[C:32]1[NH:31][CH2:30][CH2:29][N:13]1[C:14]1[S:15][C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:17]([C:19]([F:22])([F:20])[F:21])[N:18]=1

참가 물질

반응물 3

HCID 160352-Chloroethyl isocyanate

HCID 676565-Thiazolecarboxylic acid, 2-amino-4-(trifluoromethyl)-, ethyl ester

HCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylate

생성물 1

HCID 59481234Ethyl 2-(2-oxoimidazolidin-1-yl)-4-(trifluoromethyl)thiazole-5-carboxylate수율 30%

실험 절차

Following the procedure as described in Example 3, making variations as required to replace ethyl 2-amino-4-methylthiazole-5-carboxylate with ethyl 2-amino-4-(trifluoromethyl)thiazole-5-carboxylate to react with 2-chloroethyl isocyanate, the title compound was obtained as a colorless solid in 30% yield: mp 185-187° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 5.54 (s, 1H), 4.36-4.21 (m, 4H), 3.74-3.68 (m, 2H), 1.36-1.31 (m, 3H); 13C NMR (75 MHz, CDCl3) δ 159.8, 157.0, 125.4, 122.6, 121.8, 118.2, 62.0, 44.2, 43.8, 14.0; MS (ES+) m/z 310.2 (M+1).