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

HRID 2200181Notes

Reaction equation

HRID 2200181 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].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].CCOC(C)=O>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][S:23]([CH3:22])(=[O:25])=[O:24])[CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 27757093-Nitro-5-(trifluoromethyl)aniline

Product 1

HCID 68424558N-[3-nitro-5-(trifluoromethyl)phenyl]methanesulfonamideYield 36.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 3-nitro-5-(trifluoromethyl)aniline (300 mg, 1.45 mmol) in DCM (5 mL), add triethylamine (294 mg, 2.9 mmol) and then methylsulfonyl chloride (182 mg, 1.6 mmol). Stir the reaction at room temperature for 17 hrs. TLC (EtOAc:PE=1:3) shows the reaction is complete. Concentrate under reduced pressure to afford the crude product. Purification by chromatography (silica gel, EtOAc:PE=3:7) affords the title compound (150 mg, 36%).

Workup

  1. customthe reaction at room temperature for 17 hrs
  2. concentrationConcentrate under reduced pressure
  3. customto afford the crude product
  4. customPurification by chromatography (silica gel, EtOAc:PE=3:7)

Sources & evidence

ORD record
ord-72b42db2044b4c508d5ec71873d3731d
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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