Methanesulfonyl chloride → N-[3-nitro-5-(trifluoromethyl)phenyl]methanesulfonamide

HRID 1957954Notes

Reaction equation

HRID 1957954 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[NH2:7])([O-:3])=[O:2].[CH3:15][S:16](Cl)(=[O:18])=[O:17].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][S:16]([CH3:15])(=[O:18])=[O:17])[CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 27757093-Nitro-5-(trifluoromethyl)aniline

Product 1

HCID 68424558N-[3-nitro-5-(trifluoromethyl)phenyl]methanesulfonamideYield 52.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Nitro-5-trifluoromethylaniline (0.8 g; 4 mmol) was suspended in pyridine (5 mL), methanesulfonylchloride (0.6 mL; 8 mmol) was added at 0° C. and the mixture stirred for 5 hours at room temperature. A solution of sodium bicarbonate was then added to the reaction mixture and the precipitate obtained was washed with diluted hydrochloric acid and dried. 0.6 g (2.11; 52.8% yield) of N-(3-nitro-5-trifluoromethyl-phenyl)-methylsulfonamide were obtained as solid.

Workup

  1. customthe precipitate obtained
  2. washwas washed with diluted hydrochloric acid
  3. customdried

Sources & evidence

ORD record
ord-e8729bd48c984c109a2441b595edf406
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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