Phosgene → [5-(3-Chloro-benzyl)-4-methyl-thiazol-2-yl]-(4-[1,2,4]triazol-1-yl-phenyl)-amine

HRID 604870

반응식

HRID 604870 반응식
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]([NH2:15])=[S:14])=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.Cl[CH:17]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)[C:18](=O)[CH3:19].C(N(CC)C(C)C)(C)C.ClC(Cl)=O>C(O)C>[Cl:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][C:17]1[S:14][C:13]([NH:12][C:9]2[CH:8]=[CH:7][C:6]([N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)=[CH:11][CH:10]=2)=[N:15][C:18]=1[CH3:19]

참가 물질

6

반응물 4

HCID 6371Phosgene2회HCID 81531DiisopropylethylamineHCID 42509853-Chloro-4-(3-chlorophenyl)-2-butanoneHCID 52606784-(1,2,4-Triazol-1-yl)phenylthiourea

생성물 1

HCID 25106457[5-(3-Chloro-benzyl)-4-methyl-thiazol-2-yl]-(4-[1,2,4]triazol-1-yl-phenyl)-amine

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
170 °C

실험 절차

A suspension of 55 mg (0.25 mmol) 4-(1,2,4-triazol-1-yl)phenylthiourea, of 60 mg (0.28 mmol) 3-chloro-4-(3-chlorophenyl)-2-butanone and of 65 mg (0.5 mmol) N,N-diisopropyl ethyl amine in ethanol (2.5 ml) was refluxed over night. The same amount of chloro ketone was added and the reaction was heated to reflux over night. Again 1.1 equivalent of chloro ketone was added and the reaction was heated for 10 minutes in a microwave oven to 170° C. The solvent was evaporated and the residue was purified on silica gel with methylene chloride/methanol 19/1 yielding 27 mg (28%) [5-(3-chloro-benzyl)-4-methyl-thiazol-2-yl]-(4-[1,2,4]triazol-1-yl-phenyl)-amine as a yellow solid. MS ISP (m/e): 382.1 (100) (M+H)+. 1H NMR (CDCl3, 250 MHz): δ (ppm)=8.48 (s, 1H), 8.09 (s, 1H), 7.60 (d, 2H), 7.46 (d, 2H), 7.25-7.18 (m, 3H), 7.09 (d, 1H), 3.96 (s, 2H), 2.29 (s, 3H).

후처리

  1. temperaturethe reaction was heated
  2. temperatureto reflux over night
  3. customThe solvent was evaporated
  4. customthe residue was purified on silica gel with methylene chloride/methanol 19/1 yielding 27 mg (28%) [5-(3-chloro-benzyl)-4-methyl-thiazol-2-yl]-(4-[1,2,4]triazol-1-yl-phenyl)-amine as a yellow solid

출처 및 근거

ORD 기록
ord-a3be7135f3944c2087df2195ee7e0bd6
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910740B2

연결된 노트

불러오는 중…