Triethylamine → 1-(4-Chlorophenyl)-3-(4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]-2,6-dimethylphenyl)thiourea

HRID 412329노트

반응식

HRID 412329 반응식
Cl.Cl.[NH2:3][C:4]1[C:36]([CH3:37])=[CH:35][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:32]=[CH:31][C:22]([CH2:23][CH:24]5[S:28][C:27](=[O:29])[NH:26][C:25]5=[O:30])=[CH:21][CH:20]=4)[N:14]([CH3:33])[C:13]=3[CH:34]=2)=[CH:6][C:5]=1[CH3:38].[Cl:39][C:40]1[CH:45]=[CH:44][C:43]([N:46]=[C:47]=[S:48])=[CH:42][CH:41]=1.C(N(CC)CC)C>O1CCCC1>[Cl:39][C:40]1[CH:45]=[CH:44][C:43]([NH:46][C:47]([NH:3][C:4]2[C:5]([CH3:38])=[CH:6][C:7]([O:8][C:9]3[CH:10]=[CH:11][C:12]4[N:16]=[C:15]([CH2:17][O:18][C:19]5[CH:20]=[CH:21][C:22]([CH2:23][CH:24]6[S:28][C:27](=[O:29])[NH:26][C:25]6=[O:30])=[CH:31][CH:32]=5)[N:14]([CH3:33])[C:13]=4[CH:34]=3)=[CH:35][C:36]=2[CH3:37])=[S:48])=[CH:42][CH:41]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 164804-Chlorophenyl isothiocyanateHCID 16719220Efatutazone Dihydrochloride

생성물 1

HCID 103052481-(4-Chlorophenyl)-3-(4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]-2,6-dimethylphenyl)thiourea수율 63.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 5-[4-[6-(4-amino-3,5-dimethylphenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (288 mg), 4-chlorophenyl isothiocyanate (102 mg), triethylamine (121 mg) and anhydrous tetrahydrofuran (10 ml) was stirred at room temperature for 23 hours. The reaction mixture was concentrated and diluted with water. The precipitate was isolated by filtration and then chromatographed on a silica gel column using ethyl acetate:n-hexane=3:1 as the eluant to afford the title compound (215 mg, mp 160-162° C.).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. customThe precipitate was isolated by filtration
  4. customchromatographed on a silica gel column

출처 및 근거

ORD 기록
ord-6c8025d7418c40e0a804426d04de5a8e
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562849B1

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