4-Toluenesulfonyl chloride → 2-amino-3-nitro-N-tosylaniline

HRID 551016Notes

Reaction equation

HRID 551016 reaction equation
[N+:1]([C:4]1[C:5]([NH2:11])=[C:6]([NH2:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>N1C=CC=CC=1>[NH2:11][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][C:6]=1[NH:10][S:18]([C:15]1[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=1)(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 43595253-Nitro-1,2-phenylenediamine

Product 1

HCID 141475022-amino-3-nitro-N-tosylaniline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred mixture of 3-nitro-1,2-phenylenediamine (1.00 g, 6.53 mmol) and p-toluenesulfonyl chloride (1.25 g, 6.53 mmol) in pyridine (50 ml) was heated at reflux for 1 h, then concentrated to dryness in vacuo to give the title compound in sufficient purity for use in the next step. MS: m/z=308 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-cd08dc7006014e319d93bf0faed3fb97
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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