O-Phenylenediamine → 2-((4-Phenoxyphenyl)sulfonylamino)aniline

HRID 323115Notes

Reaction equation

HRID 323115 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([NH2:25])[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH2:24]>CCCCCC>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:24][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[NH2:25])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 27947564-Phenoxybenzene-1-sulfonyl chloride

Product 1

HCID 211847012-((4-Phenoxyphenyl)sulfonylamino)aniline

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The title compound was prepared according to General Method C using 4-phenoxyphenylsulfonyl chloride (969 mg, 3.6 mmol) and o-phenylenediamine (300 mg, 2.77 mmol). The reaction mixture was partitioned between water (200 ml) and toluene:methylene chloride (1:3). The organic phase collected and the methylene chloride evaporated leaving the toluene. Hexane added and the product precipatated from solution. (317 mg, 34%) EI-MS m/z 341 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between water (200 ml) and toluene:methylene chloride (1:3)
  2. customThe organic phase collected
  3. customthe methylene chloride evaporated
  4. customleaving the toluene

Sources & evidence

ORD record
ord-87aad1acaadf4e44ad12a5386ac100b1
Source dataset
uspto-grants-2001_04
Patent number
US06211373B1

Reaction notes

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