Benzenesulfonamide, 4-methyl-N-(2-methyl-4-nitrophenyl)- → HCID 869319, compound

HRID 436547Notes

Reaction equation

HRID 436547 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:12]=2[CH3:20])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[H][H]>[Ni].O1CCCC1>[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=2[CH3:20])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 4430080Benzenesulfonamide, 4-methyl-N-(2-methyl-4-nitrophenyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 869319HCID 869319, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

30.6g (0.6 mole) of 4-(N-p-toluenesulfonyl)amino-3-methyl-nitrobenzene 1g of fresh-developed Raney nickel and 60ml of tetrahydrofuran were charged into an autoclave and the autoclave was pressurized to 60kg/cm2 with hydrogen. The reaction was carried out at 50° to 100° C while stirring. After completion of the reaction, the Raney nickel was removed from the reaction solution and the tetrahydrofuran was distilled out to obtain brown 4-(N-p-toluenesulfonyl)amino-3-methylaniline. The product was recrystallized from ethyl acetate to obtain 24g of yellow-brown crystals.

Workup

  1. customwas carried out at 50° to 100° C
  2. customAfter completion of the reaction
  3. customthe Raney nickel was removed from the reaction solution
  4. distillationthe tetrahydrofuran was distilled out

Sources & evidence

ORD record
ord-acf7b979af804bbfb518364c3c5c2777
Source dataset
uspto-grants-1977_02
Patent number
US04009205

Reaction notes

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