Methyl 3-Bromopyruvate → Methyl 2-(4-phenyl-1,2,3-thiadiazol-5-yl)thiazole-4-carboxylate

HRID 1250204

반응식

HRID 1250204 반응식
[C:1]1([C:7]2[N:8]=[N:9][S:10][C:11]=2[C:12](=[S:14])[NH2:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:16][C:17](=O)[C:18]([O:20][CH3:21])=[O:19].C(=O)([O-])O.[Na+]>ClC1C=CC=CC=1>[C:1]1([C:7]2[N:8]=[N:9][S:10][C:11]=2[C:12]2[S:14][CH:16]=[C:17]([C:18]([O:20][CH3:21])=[O:19])[N:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 352524Methyl 3-BromopyruvateHCID 516892Sodium BicarbonateHCID 183275234-Phenyl-1,2,3-thiadiazole-5-carbothioamide

생성물 1

HCID 18327521Methyl 2-(4-phenyl-1,2,3-thiadiazol-5-yl)thiazole-4-carboxylate수율 48.8%

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

실험 절차

In 20 ml of chlorobenzene were dissolved 1.1 g (5.0 mmol) of 4-phenyl-1,2,3-thiadiazole-5-carbothioamide and 0.92 g (5.0 mmol) of methyl bromopyruvate. The solution thus obtained was stirred for 3 hours with heating under reflux. After the reaction was completed, the reaction mixture was cooled to room temperature, a saturated aqueous solution of sodium hydrogen carbonate was added thereto, and the objective product was extracted with ethyl acetate. The solvent was distilled off from the extract solution under a reduced pressure, and the residue was purified by silica gel column chromatography using 3:1 mixture of n-hexane and ethyl acetate. Thus, 0.74 g of the objective compound was obtained.

후처리

  1. customThe solution thus obtained
  2. temperaturewith heating
  3. temperatureunder reflux
  4. extractionthe objective product was extracted with ethyl acetate
  5. distillationThe solvent was distilled off from the extract solution under a reduced pressure
  6. customthe residue was purified by silica gel column chromatography
  7. addition3:1 mixture of n-hexane and ethyl acetate

출처 및 근거

ORD 기록
ord-d8b0bb66c694467a803ec8faffd9340d
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06337341B1

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