2-Nitrobenzenesulfonyl chloride → 2-amino-N-(5,6-dimethylpyridin-3-yl)benzenesulfonamide

HRID 1772881Notes

Reaction equation

HRID 1772881 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-])=O.[CH3:14][C:15]1[CH:16]=[C:17]([NH2:22])[CH:18]=[N:19][C:20]=1[CH3:21].Cl[Sn]Cl>N1C=CC=CC=1.C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:22][C:17]1[CH:18]=[N:19][C:20]([CH3:21])=[C:15]([CH3:14])[CH:16]=1)(=[O:12])=[O:11]

Participants

6

Reactant 3

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 24479Stannous ChlorideHCID 104191675,6-Dimethylpyridin-3-amine

Product 1

HCID 900306042-amino-N-(5,6-dimethylpyridin-3-yl)benzenesulfonamideYield 105.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

The title compound (2.7 g, 13.0 mmol) was prepared in two steps from 2-nitrobenzenesulfonyl chloride (3.20 g, 14.4 mmol) and 5,6-dimethylpyridin-3-amine (1.5 g, 12.3 mmol) in pyridine (20 mL) at rt; followed by SnCl2 (8.88 g, 46.8 mmol) in ethanol at reflux for 2 h using the methods of (IntA1), steps 1 and 2.

Workup

  1. temperatureat reflux for 2 h

Sources & evidence

ORD record
ord-c82fd4c1401b4c88b6d64a084cee90c1
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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