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

HRID 636672

Reaction equation

HRID 636672 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5de52b7505404866afc77c4c6bf0c9b3
Source dataset
uspto-grants-2001_02
Patent number
US06194444B1

Linked notes

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