p-Toluenesulfonic acid monohydrate → HCID 136335909, compound

HRID 2266451Notes

Reaction equation

HRID 2266451 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([S:17][CH:18]([C:22](=O)[CH3:23])[C:19](=O)[CH3:20])=[CH:13][CH:12]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[Cl:8][C:7]1[C:2]2[N:1]=[C:22]([CH3:23])[C:18]([S:17][C:14]3[CH:13]=[CH:12][C:11]([Cl:10])=[CH:16][CH:15]=3)=[C:19]([CH3:20])[C:3]=2[C:4]([OH:9])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 7226463-[(4-Chlorophenyl)sulfanyl]pentane-2,4-dioneHCID 50700783-Amino-4-chlorophenol

Product 1

HCID 136335909HCID 136335909, compound

Conditions

Temperature
140 °C

Procedure

A mixture of 3-amino-4-chlorophenol (5.0 g), 3-(4-chlorophenylsulfanyl)pentane-2,4-dione (8.4 g), p-toluenesulfonic acid monohydrate (12 g) was heated at 140° C. for 6 hours. The mixture was cooled to room temperature and purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 1:1 by volume) to afford title compound as a brown solid, 1.3 g.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompurified by column chromatography on silica gel
  3. washeluting with a mixture of dichloromethane and ethyl acetate (1:0 to 1:1 by volume)

Sources & evidence

ORD record
ord-15674b51fc7c4322ba05ea973289d51b
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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