Benzenesulfonyl chloride, 4-chloro-3-nitro- → Benzenesulfonamide, 4-chloro-N-methyl-3-nitro-N-phenyl-

HRID 1968676Notes

Reaction equation

HRID 1968676 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.[CH3:22][NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:23]([CH3:22])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 7515N-MethylanilineHCID 8471Triethylamine

Product 1

HCID 80850Benzenesulfonamide, 4-chloro-N-methyl-3-nitro-N-phenyl-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Chloro-3-nitrobenzene-1-sulfonyl chloride (10.6 g, 0.041 mol) was dissolved in toluene (50 ml); and triethylamine (4.14 g, 0.041 mol) was then added. To the resulting solution, N-methylaniline (4.4 g, 0.041 mol) was added under stirring. The reaction mixture was incubated at 70-80° C. for 1 h. Thereafter, it was allowed to cool. The cooled solution was washed twice with 30 ml of water and concentrated under vacuum. The residue was recrystallized from ethanol. The yield of 4-chloro-N-methyl-3-nitro-N-phenylbenzene sulfonamide was 9.4 g (61%).

Workup

  1. temperatureto cool
  2. washThe cooled solution was washed twice with 30 ml of water
  3. concentrationconcentrated under vacuum
  4. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-43d316601ce7404bbe6910764e986f1f
Source dataset
uspto-grants-2013_04
Patent number
US08426433B2

Reaction notes

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