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

HRID 652063Notes

Reaction equation

[CH3:1][N:2]1[C:9](=[O:10])[CH2:8][C:6](=[O:7])[N:5]([CH3:11])[C:3]1=[S:4].N1C=CC=CC=1.Cl[C:19](OCC)=[O:20].[Cl:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[C:27]([O:32][C:33]2[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=2[Cl:40])[CH:26]=1>CN(C)C1C=CN=CC=1.ClCCl.C(O)C.CN(C)C=O>[CH3:11][N:5]1[C:6](=[O:7])[CH:8]([C:19](=[O:20])[NH:29][C:28]2[CH:30]=[CH:31][C:25]([Cl:24])=[CH:26][C:27]=2[O:32][C:33]2[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=2[Cl:40])[C:9](=[O:10])[N:2]([CH3:1])[C:3]1=[S:4]

Participants

Conditions

Temperature: 0 °C

Procedure

15.5 g (0.09 mol) of 1,3-dimethyl-2-thiobarbituric acid, 8.8 g (1.1 mol) of pyridine and 0.9 g of 4-dimethylaminopyridine are dissolved in 65 ml of dichloromethane and the solution is cooled to 0° C. Then 10.2 g (0.094 mol) of ethyl chloroformate are added dropwise over 1 hours. The mixture is stirred for 12 hours at 0° C. and then for 7 hours at room temperature. The bulk of the solvent is evaporated off, a solution of 26.1 g (0.09 mol) of 4-chloro-2-(2,6-dichlorophenoxy)aniline in 360 ml of ethanol and 30 ml of dimethylformamide is added and the mixture is boiled under reflux with stirring for 6 hours. The reaction mixture is then cooled and the resultant crystalline precipitate is isolated by filtration and, if necessary, is recrystallised from dioxane/ethanol. Melting point 254°-257° C.

Workup

waitfor 7 hours at room temperature
customThe bulk of the solvent is evaporated off
temperatureunder reflux
stirringwith stirring for 6 hours
temperatureThe reaction mixture is then cooled
customthe resultant crystalline precipitate is isolated by filtration
customif necessary, is recrystallised from dioxane/ethanol

Sources & evidence

ORD record: ord-39cabadf08414dbbb2f769039c80f6b9
Source dataset: uspto-grants-1987_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04670441

Reaction notes

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