Pyridine → HCID 14421725, compound

HRID 746200Notes

Reaction equation

HRID 746200 reaction equation
C(CN[NH:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)C1C=CC=CC=1.[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[N:30]1C=CC=C[CH:31]=1>>[CH3:31][NH:30][C:15]1[CH:16]=[C:11]([NH:10][S:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:28])=[O:27])[CH:12]=[CH:13][C:14]=1[N+:17]([O-:19])=[O:18]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 86740925HCID 86740925, compound

Product 1

HCID 14421725HCID 14421725, compoundYield 98%

Procedure

2.5 g (9.7 mmol) of 3-(N-benzylmethylamino-4-nitroaniline in 15 ml dry pyridine was treated with 1.5 ml of benzenesulphonyl chloride at 0° C. and the mixture was then allowed to warm slowly to room temperature. After 3 h the pyridine was removed under vacuum and the residue was dissolved in 100 ml of 2N HCl in 65% aqueous ethanol. The mixture was then heated under reflux until only one compound was seen by TLC (CHCl3 --MeOH, 9:1). Concentration of the solution then gave crystals of N-(3-methylamino-4-nitrophenyl)benzenesulphonamide 2.93 g, 98%, m.p. 172°-173.5° C.

Workup

  1. customAfter 3 h the pyridine was removed under vacuum
  2. dissolutionthe residue was dissolved in 100 ml of 2N HCl in 65% aqueous ethanol
  3. temperatureThe mixture was then heated
  4. temperatureunder reflux until only one compound

Sources & evidence

ORD record
ord-adda3aae7b1e42989a03a363eeb805b3
Source dataset
uspto-grants-1986_07
Patent number
US04603125

Reaction notes

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