2-Mercaptobenzoic Acid → HCID 11197435, compound

HRID 1609270Notes

Reaction equation

HRID 1609270 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].C(=O)([O-])[O-].[K+].[K+].F[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25].[CH2:27](I)[CH3:28]>CN(C)C=O>[N+:24]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[S:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH2:27][CH3:28])=[O:9])([O-:26])=[O:25]

Participants

6

Reactant 4

HCID 54432-Mercaptobenzoic AcidHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 11197435HCID 11197435, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In 100 ml of N,N-dimethylformamide was dissolved 15.4 g of thiosalicylic acid followed by addition of 42 g of potassium carbonate and 14.8 g of 2-fluoronitrobenzene, and the mixture was stirred at 100° C. for 3 hours. After the reaction mixture had cooled to room temperature, 18.7 g of ethyl iodide was added thereto and the mixture was further stirred at room temperature for 3 hours. The reaction mixture was then poured into ice-water and extracted with ether. The ether layer was washed with water twice, dried and concentrated. Finally the residue was crystallized from ethanol to give 25.5 g of the title compound as yellow crystals.

Workup

  1. temperatureAfter the reaction mixture had cooled to room temperature
  2. stirringthe mixture was further stirred at room temperature for 3 hours
  3. extractionextracted with ether
  4. washThe ether layer was washed with water twice
  5. customdried
  6. concentrationconcentrated
  7. customFinally the residue was crystallized from ethanol

Sources & evidence

ORD record
ord-438bbeb97d6e4aa189132c8351edb588
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

Loading…