p-Toluenesulfonic acid → 4-{[3-Methoxy-5-(trifluoromethyl)phenyl]amino}-3-penten-2-one

HRID 1268887Notes

Reaction equation

HRID 1268887 reaction equation
[C:1]([CH2:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1)[NH2:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([NH:13][C:5]([CH3:6])=[CH:4][C:1](=[O:3])[CH3:2])[CH:14]=[C:15]([C:17]([F:18])([F:20])[F:19])[CH:16]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31261AcetylacetoneHCID 6056715-(Trifluoromethyl)-m-anisidine

Product 1

HCID 694553434-{[3-Methoxy-5-(trifluoromethyl)phenyl]amino}-3-penten-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.57 g (15.7 mmol) Acetylacetone, 3.00 g (15.7 mmol) 3-methoxy-5-(trifluoromethyl)aniline, and 0.1 g (1.6 mmol) 4-toluenesulfonic acid are dissolved in 150 ml toluene. The reaction mixture is refluxed for 7 h with a Dean-Stark trap to remove water. After cooling down to room temperature, the suspension is filtered. The solid is purified by recrystallisation from ethanol.

Workup

  1. temperatureThe reaction mixture is refluxed for 7 h with a Dean-Stark trap
  2. customto remove water
  3. filtrationthe suspension is filtered
  4. customThe solid is purified by recrystallisation from ethanol

Sources & evidence

ORD record
ord-76713dd44a004bd3b44883728ad35591
Source dataset
uspto-grants-2007_04
Patent number
US07199136B2

Reaction notes

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