Epichlorohydrin → 4-(3-Chloro-phenyl)-2-(6-oxiranylmethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide

HRID 1667756

반응식

HRID 1667756 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([N:16]3[C:20]4[CH:21]=[C:22]([OH:25])[CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[S:11][C:12]=2[C:13]([NH2:15])=[O:14])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:33][CH:34]1[CH2:36][O:35]1>[I-].[K+].CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([N:16]3[C:20]4[CH:21]=[C:22]([O:25][CH2:33][CH:34]5[CH2:36][O:35]5)[CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[S:11][C:12]=2[C:13]([NH2:15])=[O:14])[CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 674454984-(3-Chloro-phenyl)-2-(6-hydroxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide

생성물 1

HCID 866428344-(3-Chloro-phenyl)-2-(6-oxiranylmethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide수율 75%

시약·촉매·용매 2

HCID 4875Potassium Iodide촉매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 0.037 g (0.1 mmole) of 4-(3-chloro-phenyl)-2-(6-hydroxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide (I.25d), 0.5 mL of dimethylformamide, 0.069 g (0.5 mmole) of potassium carbonate, 0.001 g of potassium iodide and 0.012 mL (0.15 mmole) of 2-chloromethyl-oxirane was heated at 100 degrees for 3 hours. The mixture was concentrated under reduced pressure, diluted with 20 mL of water and the resulting precipitate collected by filtration. The solid was triturated with diethyl ether to give 0.032 g of 4-(3-chloro-phenyl)-2-(6-oxiranylmethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide (I.39a) as a white solid.

후처리

  1. temperaturewas heated at 100 degrees for 3 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additiondiluted with 20 mL of water
  4. filtrationthe resulting precipitate collected by filtration
  5. customThe solid was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-43e8fccbc30f4b768f6fca37b6fdf341
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044213B2

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