p-Toluenesulfonic acid monohydrate → HCID 136335905, compound

HRID 2266462Notes

Reaction equation

HRID 2266462 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:10][S:11]([C:14]1[CH:27]=[CH:26][C:17]([CH2:18][CH:19]([C:23](=O)[CH3:24])[C:20](=O)[CH3:21])=[CH:16][CH:15]=1)(=[O:13])=[O:12].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[Cl:8][C:7]1[C:2]2[N:1]=[C:23]([CH3:24])[C:19]([CH2:18][C:17]3[CH:16]=[CH:15][C:14]([S:11]([CH3:10])(=[O:13])=[O:12])=[CH:27][CH:26]=3)=[C:20]([CH3:21])[C:3]=2[C:4]([OH:9])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 50700783-Amino-4-chlorophenolHCID 68786995HCID 68786995, compound

Product 1

HCID 136335905HCID 136335905, compound

Conditions

Temperature
160 °C

Procedure

A mixture of 3-amino-4-chlorophenol (0.36 g), 3-(4-methanesulfonylbenzyl)pentane-2,4-dione (0.5 g) and p-toluenesulfonic acid monohydrate (0.05 g) was heated at 160° C. for 2.5 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 (50:1 to 2:1 by volume) to afford title compound (7:10 mixture of keto-enol tautomers) as a beige solid, 0.32 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 (50:1 to 2:1 by volume)

Sources & evidence

ORD record
ord-f6e244d20b2b4d60a5d9d15e5703a214
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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