4-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}aniline → 1,3-Dimethyl-5-[4-(5-trifluoromethylpyrid-2-yloxy)phenylcarbamoyl]-2-thiobarbituric acid

HRID 652061Notes

Reaction equation

HRID 652061 reaction equation
[CH3:1][N:2]1[C:9](=[O:10])[CH:8]([C:11]([O:13]CC)=O)[C:6](=[O:7])[N:5]([CH3:16])[C:3]1=[S:4].[F:17][C:18]([F:34])([F:33])[C:19]1[CH:20]=[CH:21][C:22]([O:25][C:26]2[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=2)=[N:23][CH:24]=1>CN(C)C=O>[CH3:16][N:5]1[C:6](=[O:7])[CH:8]([C:11](=[O:13])[NH:30][C:29]2[CH:31]=[CH:32][C:26]([O:25][C:22]3[CH:21]=[CH:20][C:19]([C:18]([F:34])([F:17])[F:33])=[CH:24][N:23]=3)=[CH:27][CH:28]=2)[C:9](=[O:10])[N:2]([CH3:1])[C:3]1=[S:4]

Participants

4

Reactant 2

HCID 27830854-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}anilineHCID 140533471,3-Dimethyl-5-ethoxycarbonyl-2-thiobarbituric acid

Product 1

HCID 140533611,3-Dimethyl-5-[4-(5-trifluoromethylpyrid-2-yloxy)phenylcarbamoyl]-2-thiobarbituric acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.5 g (10 mmol) of 1,3-dimethyl-5-ethoxycarbonyl-2-thiobarbituric acid, 2,55 g (10 mmol) of 4-(5-trifluoromethylpyrid-2-yloxy)aniline and 5 ml of dimethylformamide are stirred for 6 hours at 118° C. The reaction mixture is then cooled, triturated with water and the crystalline precipitate is isolated by filtration. The crude product is recrystallised from ethanol. Melting point 156°-158° C.

Workup

  1. temperatureThe reaction mixture is then cooled
  2. customtriturated with water
  3. customthe crystalline precipitate is isolated by filtration
  4. customThe crude product is recrystallised from ethanol

Sources & evidence

ORD record
ord-1ece00a06c314f4e802ebf7efa6ecb2e
Source dataset
uspto-grants-1987_06
Patent number
US04670441

Reaction notes

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