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

HRID 636672

反応式

HRID 636672 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5de52b7505404866afc77c4c6bf0c9b3
出典データセット
uspto-grants-2001_02
特許番号
US06194444B1

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