m-Toluidine → 4-(3-Methylanilino)pyridine-3-sulfonamide--hydrogen chloride (1/1)

HRID 2225014Notes

Reaction equation

HRID 2225014 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1>C(O)CCC>[ClH:1].[CH3:19][C:15]1[CH:14]=[C:13]([NH:12][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[S:8]([NH2:11])(=[O:10])=[O:9])[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7934m-ToluidineHCID 1184264-Chloro-3-pyridinesulphonamide

Product 1

HCID 534068664-(3-Methylanilino)pyridine-3-sulfonamide--hydrogen chloride (1/1)Yield 98%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A 2-L, three-necked flask equipped with mechanical stirrer, thermometer and condenser was charged with 4-chloro-3-pyridinesulfonamide I (300.0 g, 1.56 mol), m-toluidine (200.3 g, 1.87 mol) and 1200 mL n-butanol. The reaction mixture was heated for 2-4 hours and then cooled to room temperature. The solid was filtered and washed with n-butanol. After drying, 4-[(3-methylphenyl)amino]-3-pyridinesulfonamide hydrochloride (457.1 g, 98%) was obtained as pale-yellow solid having a purity of 99.96% by HPLC.

Workup

  1. temperatureThe reaction mixture was heated for 2-4 hours
  2. filtrationThe solid was filtered
  3. washwashed with n-butanol
  4. customAfter drying

Sources & evidence

ORD record
ord-9fd50ea955f5411b9442e8bb49a9a00f
Source dataset
uspto-grants-2008_05
Patent number
US07378527B2

Reaction notes

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