Chloroform → 4-Nitrophenyl (7-Isopropoxycarbonyl-6-methyl-2,3,5,6-tetrahydropyrrolo[2,1-b]thiazol-3-ylidene)acetate

HRID 2372377Notes

Reaction equation

HRID 2372377 reaction equation
[CH3:1][CH:2]1[CH2:6][NH:5][C:4](=[S:7])[CH:3]1[C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9].C([O-])(=O)C.[Na+].Br[CH2:20][C:21](=O)[CH2:22][C:23]([O:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)=[O:24].C(Cl)(Cl)Cl>C1C=CC=CC=1>[CH:11]([O:10][C:8]([C:3]1[CH:2]([CH3:1])[CH2:6][N:5]2[C:21](=[CH:22][C:23]([O:25][C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=3)=[O:24])[CH2:20][S:7][C:4]=12)=[O:9])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 517045Sodium AcetateHCID 10465433Isopropyl 4-Methyl-2-thioxopyrrolidine-3-carboxylateHCID 19903380HCID 19903380, compound

Product 1

HCID 867455674-Nitrophenyl (7-Isopropoxycarbonyl-6-methyl-2,3,5,6-tetrahydropyrrolo[2,1-b]thiazol-3-ylidene)acetateYield 66.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

8.9 g of isopropyl 4-methyl-2-thioxopyrrolidine-3-carboxylate was dissolved in 200 ml of benzene and 5.1 g of anhydrous sodium acetate and 16.7 g of 4-nitrophenyl 4-bromoacetoacetate were added thereto. The obtained mixture was stirred at room temperature for 8 hours. Then 500 ml of chloroform was added and the mixture was washed with water and a saturated aqueous solution of sodium chloride. After drying and distilling off the solvent, the obtained residue was purified by silica gel column chromatography. A fraction eluted with dichloromethane was crystallized from a mixture of ether and n-hexane. Thus 11.9 g of the title compound was obtained.

Workup

  1. washthe mixture was washed with water
  2. customAfter drying
  3. distillationdistilling off the solvent
  4. customthe obtained residue was purified by silica gel column chromatography
  5. washA fraction eluted with dichloromethane
  6. customwas crystallized from a mixture of ether and n-hexane

Sources & evidence

ORD record
ord-ca74665c805842a6a1a8e71e7009738f
Source dataset
uspto-grants-1992_03
Patent number
US05098919

Reaction notes

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