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Thiourea → Ethyl 2-amino-5-benzyl-1,3-thiazole-4-carboxylate

HRID 1246498
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HRID 1246498 반응식
Br[CH:2]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:17][C:18]([NH2:20])=[S:19]>CCO>[NH2:20][C:18]1[S:19][C:2]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:17]=1
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참가 물질

4

반응물 2

HCID 2723790ThioureaHCID 10755525Ethyl 3-bromo-2-oxo-4-phenylbutanoate

생성물 1

HCID 12603729Ethyl 2-amino-5-benzyl-1,3-thiazole-4-carboxylate수율 15.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Ethyl 3-bromo-2-oxo-4-phenylbutanoate (5.8 g) was dissolved in EtOH (110 ml), and then thiourea (3.1 g) was added to the solution. The reaction mixture was refluxed for 2 hours under N2 atmosphere. The cooled reaction mixture was evaporated in vacuo. The residual solid was suspended (pH=8) in saturated NaHCO3 and water. The solid was collected by filtration, and purified by flash column chromatography over silica gel with CHCl3/MeOH (10:1) as an eluent to give ethyl 2-amino-5-benzyl-1,3-thiazole-4-carboxylate (808.2 mg) as a yellow wax.

후처리

  1. temperatureThe reaction mixture was refluxed for 2 hours under N2 atmosphere
  2. customThe cooled reaction mixture
  3. customwas evaporated in vacuo
  4. filtrationThe solid was collected by filtration
  5. custompurified by flash column chromatography over silica gel with CHCl3/MeOH (10:1) as an eluent

출처 및 근거

ORD 기록
ord-500a526f3be64f21868c112588ea11d7
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07125901B2

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