Ammonia → HCID 18536569, compound

HRID 1885855Notes

Reaction equation

HRID 1885855 reaction equation
[CH3:1][S:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.S(Cl)(Cl)=O.[NH3:19]>C1C=CC=CC=1>[CH3:1][S:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:19])=[O:8])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 13988043HCID 13988043, compound

Product 1

HCID 18536569HCID 18536569, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred solution of 4-methylthio-2-nitrobenzoic acid (4.56 g) and thionyl chloride (2.77 g) in benzene (65 ml) was heated under reflux for 1.5 hours. Aqueous ammonia (10 ml) was added dropwise to the stirred cooled (<5° C.) reaction mixture, which was then stirred with cooling for 45 minutes. Benzene was removed under reduced pressure and the residual solid was washed with water and recrystallised to yield 4-methylthio-2-nitrobenzamide, (2.35 g), m.p. 176°-8° C.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. temperaturecooled
  3. custom(<5° C.) reaction mixture, which
  4. temperaturewith cooling for 45 minutes
  5. customBenzene was removed under reduced pressure
  6. washthe residual solid was washed with water
  7. customrecrystallised

Sources & evidence

ORD record
ord-62f64d7b32fc49b5a9083c873189ffda
Source dataset
uspto-grants-1992_09
Patent number
US05147875

Reaction notes

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