홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

3-(Bromoacetyl)benzoic acid → 4-(3-Carboxyacetyl-phenyl)-thiazole-2-carboxylic acid ethyl ester

HRID 1266780
노트
인쇄 미리보기

반응식

HRID 1266780 반응식
[CH2:1]([O:3][C:4]([C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17](Cl)=[O:18])[CH:12]=2)[N:10]=1)=[O:5])[CH3:2].Br[CH2:21][C:22]([C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([OH:29])=[O:28])=O.C(OCC)(=S)C(N)=O>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17](=[O:18])[CH2:26][C:27]([OH:29])=[O:28])[CH:12]=2)[N:10]=1)=[O:5])[CH3:2].[CH2:1]([O:3][C:4]([C:6]1[S:7][CH:21]=[C:22]([C:24]2[CH:32]=[CH:31][CH:30]=[C:26]([C:27]([OH:29])=[O:28])[CH:25]=2)[N:10]=1)=[O:5])[CH3:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 27568353-(Bromoacetyl)benzoic acidHCID 216137632-ethoxy-2-thioxoAcetamideHCID 865869654-(3-Chlorocarbonyl-phenyl)-thiazole-2-carboxylic acid ethyl ester

생성물 2

HCID 697808034-(3-Carboxyacetyl-phenyl)-thiazole-2-carboxylic acid ethyl esterHCID 697810514-(3-Carboxy-phenyl)-thiazole-2-carboxylic acid ethyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

The 4-(3-carboxyacetyl-phenyl)-thiazole-2-carboxylic acid ethyl ester was prepared from 4-(3-chlorocarbonyl-phenyl)-thiazole-2-carboxylic acid ethyl ester [prepared by the following sequence: i.) A mixture of 3-(2-bromo-acetyl)-benzoic acid [CAS-no. 62423-73-8] (2.43 g) and ethyl thiooxamate [CAS-no. 16982-21-1] (1.6 g) in THF (40 mL) was heated to 60° C. for 4 h and then partitioned between EtOAc and brine. The organic layer was dried and evaporated and the residue was crystallized from EtOAc/hexane to give 4-(3-carboxy-phenyl)-thiazole-2-carboxylic acid ethyl ester (2.2 g) as off-white crystals, mp 225-228° C. ii.) This carboxylic acid (2.1 g) was heated with thionyl chloride in toluene and the resulting carboxylic acid chloride was used directly in the next step.] (2.24 g) and bis(trimethylsilyl)malonate with n-BuLi in ether at −60° C. to 0° C. according to general procedure K (method c2). The crude material was transformed into the title compound by stirring in isopropenyl acetate and conc. H2SO4 according to general procedure L (method a). Obtained as yellow oil (2.7 g).

후처리

  1. customprepared by the following sequence
  2. custompartitioned between EtOAc and brine
  3. customThe organic layer was dried
  4. customevaporated
  5. customthe residue was crystallized from EtOAc/hexane

출처 및 근거

ORD 기록
ord-a7b9dea0ca6f41308d72dee6aceaf3ba
출처 데이터셋
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06548495B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트