Hydrochloric Acid → HCID 67040890, compound

HRID 605064Notes

Reaction equation

HRID 605064 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C)C=O.C(OCC)(=O)C>[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[N+:11]([O-:13])=[O:12])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 73204-Chloro-3-nitrobenzoic acidHCID 10796Cesium carbonateHCID 145104-Aminothiophenol

Product 1

HCID 67040890HCID 67040890, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-chloro-3-nitrobenzoic acid (2.00 g, 10.0 mmol), 4-aminothiophenol (10.0 mmol), and cesium carbonate (6.52 g, 20.0 mmol) in anhydrous N,N-dimethylformamide (10 mL) was heated at 90° C. under a nitrogen atmosphere for 2 hours. The reaction was cooled to room temperature and poured into 50 mL of ice water and ethyl acetate (100 mL). The mixture was stirred while adjusting the pH to 2 with concentrated hydrochloric acid. The layers were separated and the organic phase washed with water (2×50 mL) and brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation in vacuo. The residue was co-evaporated with methylene chloride/hexanes and the residue triturated with methylene chloride to provide the title compound as a dark yellow solid (2.115 g, 73%).

Workup

  1. customThe layers were separated
  2. washthe organic phase washed with water (2×50 mL) and brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation in vacuo
  6. customthe residue triturated with methylene chloride

Sources & evidence

ORD record
ord-aec467d131014a429799c12633336968
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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