Water → HCID 18953300, compound

HRID 1491583Notes

Reaction equation

HRID 1491583 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([N+]([O-])=O)[CH:3]=1.[C:15]1([SH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:15]1([S:21][C:4]2[CH:3]=[C:2]([S:21][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:11]=[CH:10][C:5]=2[C:6]([O:8][CH3:9])=[O:7])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 39135Methyl 4-chloro-2-nitrobenzoate

Product 1

HCID 18953300HCID 18953300, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 4-chloro-2-nitrobenzoate (25 g), thiophenol (20.4 g) and potassium carbonate (17.6 g) in N,N-dimethylformamide was stirred at 120° C. for five hours. Water was added and the mixture extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulphate, filtered and evaporated. The product was recrystallised from cyclohexane to give 3.0 g of methyl 2,4-bis(phenylsulphenyl)benzoate as a beige solid, m.p. 123.9° C.

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe product was recrystallised from cyclohexane

Sources & evidence

ORD record
ord-dedfce3d16b74b22bbeb39beed5567cc
Source dataset
uspto-grants-1994_12
Patent number
US05371064

Reaction notes

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