4-Amino-N-(2-methylphenyl)benzenesulfonamide → HCID 47062676, compound

HRID 1186644Notes

Reaction equation

HRID 1186644 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][CH:35]=[CH:34][C:33]=2C)(=[O:30])=[O:29])=[CH:24][CH:23]=1)([O-:21])=[O:20].[B-].[Na+].[CH3:41][OH:42].C1[CH2:47][O:46]CC1>O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:41][O:42][C:26]1[CH:27]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=[CH:24][C:25]=1[S:28]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([O:46][CH3:47])=[CH:34][CH:33]=1)(=[O:30])=[O:29]

Participants

6

Reactant 4

HCID 5935694-Amino-N-(2-methylphenyl)benzenesulfonamideHCID 779038HCID 779038, compoundHCID 21899815MeOH tetrahydrofuranHCID 22959485Vertellus

Product 1

HCID 47062676HCID 47062676, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 11791229Dichloronickel;hexahydrateCatalyst

Procedure

4-Amino-N-o-tolyl-benzenesulfonamide (12a) (RK1-1-24) I To a solution of 4-Nitro-N-o-tolyl-benzenesulfonamide (11a) in 4.0 mL of a 1:1 MeOH/THF mixture, was added nickel chloride hexahydrate (163 mg, 0.68 mmol) at 0° C. under constant stirring. Sodium borohydrate (52 mg, 1.37 mmol) was added portion wise and the progress of the reaction monitored by TLC (60% hexanes/40% ethylacetate). The solvent was removed in vacuo and the remaining black solid was re-suspended in EtOAc and filtered using a pad of celite and washed with EtOAc until the filtrate, when visualized under UV light, showed no product. The solvent was removed under vacuum affording the title compound as an off-white solid (0.045 g, 100%). 1H NMR (400 MHz, CDCl3) δ 7.41 (d, J=8.8 Hz, 2H), 7.24 (d, J=8.0 Hz, 1H), 7.05 (td, J=2.0, 2.4, 2.4 Hz, 1H), 7.01-6.95 (m, 2H), 6.50 (d, J=8.8 Hz, 2H), 6.35 (br s, 1H), 4.05 (br s, 2H), 1.95 (s, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationfiltered
  3. washwashed with EtOAc until the filtrate, when
  4. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-1b4cf61ee131475da5c17c08f476ea44
Source dataset
uspto-grants-2014_03
Patent number
US08673910B2

Reaction notes

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