Ethyl bromopyruvate → 3-(2-Nitro-phenyl)-imidazo[2,1-b]thiazole-6-carboxylic acid ethyl ester

HRID 419874

반응식

HRID 419874 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[C:12]([NH2:15])[S:13][CH:14]=1)([O-:3])=[O:2].Br[CH2:17][C:18](=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(C(C)=O)C>[CH2:22]([O:21][C:19]([C:18]1[N:15]=[C:12]2[N:11]([CH:17]=1)[C:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])=[CH:14][S:13]2)=[O:20])[CH3:23]

참가 물질

4

반응물 2

HCID 66144Ethyl bromopyruvate2회HCID 5957794-(2-Nitrophenyl)thiazole-2-amine

생성물 1

HCID 596802093-(2-Nitro-phenyl)-imidazo[2,1-b]thiazole-6-carboxylic acid ethyl ester수율 52.5%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

4-(2-Nitro-phenyl)-thiazol-2-ylamine (1.60 g, 7.2 mmol) was mixed with 50 mL of methyl ethyl ketone along 0.90 mL of ethyl bromopyruvate (7.2 mmol) and stirred under reflux for 24 hours. Another equivalent of ethyl bromopyruvate (0.90 mL, 7.2 mmol) was added and the reaction mixture was stirred under reflux for another 8 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by chromatography (Isco, gradient elution, CH2Cl2 to 95% CH2Cl2, 5% MeOH) to afford 1.2 g of 3-(2-nitro-phenyl)-imidazo [2,1-b]thiazole-6-carboxylic acid ethyl ester (52% yield).

후처리

  1. temperatureunder reflux for 24 hours
  2. stirringthe reaction mixture was stirred
  3. temperatureunder reflux for another 8 hours
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography (Isco, gradient elution, CH2Cl2 to 95% CH2Cl2, 5% MeOH)

출처 및 근거

ORD 기록
ord-aeb4dd3180be41eb8e48cd2eab8a994f
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093401B2

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