Benzenesulfonamide, N-(4-methylphenyl)-4-nitro- → 4-Amino-N-(4-methylphenyl)benzenesulfonamide

HRID 1186645Notes

Reaction equation

HRID 1186645 reaction equation
NC1C=CC(S(NC2C=CC=CC=2C)(=O)=O)=CC=1.[N+:19]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:30])=[O:29])=[CH:24][CH:23]=1)([O-])=O>>[NH2:19][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 293081Benzenesulfonamide, N-(4-methylphenyl)-4-nitro-HCID 5935694-Amino-N-(2-methylphenyl)benzenesulfonamide

Product 1

HCID 5721024-Amino-N-(4-methylphenyl)benzenesulfonamideYield 99%

Procedure

(RK1-1-30)I This compound was prepared according to the procedure for compound 12a except using 11d to obtain the required product as an off-white solid (225 mg, 99%). Mp=174-176° C. (lit 190-190.5° C., Bioorganic and Medicinal Chemistry 15(2), 1014-1021; 2007); 1H NMR (400 MHz, CDCl3) δ 7.43 (d, J=8.8 Hz, 2H), 6.96 (d, J=8.4 Hz, 2H), 6.86 (d, J=8.4 Hz, 2H), 6.52 (d, J=8.8 Hz, 2H), 6.14 (br s, 1H), 4.00 (br s, 2H), 2.20 (s, 3H).

Workup

  1. custom(RK1-1-30)I This compound was prepared

Sources & evidence

ORD record
ord-5f1b80220ada47d2a5f9414f23713afa
Source dataset
uspto-grants-2014_03
Patent number
US08673910B2

Reaction notes

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