Ethanol → 1,3-Dimethyl-5-[4-chloro-2-(2,6-dichlorophenoxy)phenylcarbamoyl]-2-thiobarbituric acid

HRID 652060Notes

Reaction equation

HRID 652060 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].[Cl:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[C:20]([O:25][C:26]2[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=2[Cl:33])[CH:19]=1.C(O)C>CN(C)C=O>[CH3:16][N:5]1[C:6](=[O:7])[CH:8]([C:11](=[O:13])[NH:22][C:21]2[CH:23]=[CH:24][C:18]([Cl:17])=[CH:19][C:20]=2[O:25][C:26]2[C:27]([Cl:33])=[CH:28][CH:29]=[CH:30][C:31]=2[Cl:32])[C:9](=[O:10])[N:2]([CH3:1])[C:3]1=[S:4]

Participants

5

Reactant 3

HCID 702EthanolHCID 140533471,3-Dimethyl-5-ethoxycarbonyl-2-thiobarbituric acidHCID 140533484-Chloro-2-(2,6-dichlorophenoxy)aniline

Product 1

HCID 140533491,3-Dimethyl-5-[4-chloro-2-(2,6-dichlorophenoxy)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, 2.9 g (10 mmol) of 4-chloro-2-(2,6-dichlorophenoxy)aniline, 40 ml of ethanol and 3 ml of dimethylformamide are mixed and then boiled under reflux with stirring for 6 hours. The reaction mixture is then cooled and the resultant crystalline precipitate is isolated by filtration. If necessary, the crystalline precipitate can be recrystallised from a mixture of dioxane and ethanol. Melting point 254°-257° C.

Workup

  1. temperatureunder reflux
  2. temperatureThe reaction mixture is then cooled
  3. customthe resultant crystalline precipitate is isolated by filtration
  4. customIf necessary, the crystalline precipitate can be recrystallised from a mixture of dioxane and ethanol

Sources & evidence

ORD record
ord-3a5c48c155c54b1cb3cc92ad34110ef5
Source dataset
uspto-grants-1987_06
Patent number
US04670441

Reaction notes

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