Water → HCID 10634501, compound

HRID 399717Notes

Reaction equation

HRID 399717 reaction equation
[F-].[K+].C(O[C:6](=[O:15])[C:7](Br)([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])C.[SH:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19].O>CN(C)C=O>[CH2:11]([O:10][C:8]([C:7]1([CH3:13])[C:6](=[O:15])[NH:19][C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[S:16]1)=[O:9])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 87132-AminothiophenolHCID 94944Diethyl bromomethylmalonateHCID 522689Potassium Fluoride

Product 1

HCID 10634501HCID 10634501, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of KF (3.016 g, 52 mmoles) in anhydrous dimethyl formamide (14 ml), diethyl-2-bromo-2-methyl-malonate (3.90 ml, 20 mmoles) was added and the mixture was stirred for 15 minutes at room temperature. Subsequently, 2-mercaptoaniline (2.50 g, 20 mmoles) was added and the mixture was stirred for 6 hours at the temperature of 60° C. and overnight at room temperature. The reaction mixture was admixed with a mixture of water and ice (80 ml), the product which separated was filtered off by suction and recrystallized from absolute ethanol. Thus there were obtained 3.80 g (75.7%) of the title product in the form of white crystals, m.p. 109°-111° C.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 6 hours at the temperature of 60° C. and overnight at room temperature
  3. customthe product which separated
  4. filtrationwas filtered off by suction
  5. customrecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-4ab9aadfe4ee4bba888cb6956f68880d
Source dataset
uspto-grants-1998_10
Patent number
US05824652

Reaction notes

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