Triethylamine → 1,3-Dimethyl-4,6-dioxo-2-thioxo-N-[4-(4-trifluoromethylphenoxy)phenyl]perhydropyrimidine-5-carboxamide

HRID 1194657Notes

Reaction equation

HRID 1194657 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]=[C:15]=[O:16])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[CH3:21][N:22]1[C:29](=[O:30])[CH2:28][C:26](=[O:27])[N:25]([CH3:31])[C:23]1=[S:24].C(N(CC)CC)C>C1C=CC=CC=1>[CH3:31][N:25]1[C:26](=[O:27])[CH:28]([C:15]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([O:7][C:6]3[CH:17]=[CH:18][C:3]([C:2]([F:19])([F:20])[F:1])=[CH:4][CH:5]=3)=[CH:9][CH:10]=2)=[O:16])[C:29](=[O:30])[N:22]([CH3:21])[C:23]1=[S:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5989481,3-Dimethyl-2-sulfanylidene-1,3-diazinane-4,6-dioneHCID 131894424-(4'-Trifluoromethylphenoxy)phenyl isocyanate

Product 1

HCID 140533731,3-Dimethyl-4,6-dioxo-2-thioxo-N-[4-(4-trifluoromethylphenoxy)phenyl]perhydropyrimidine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-(4'-Trifluoromethylphenoxy)phenyl isocyanate (3.7 g.) was added to a stirred mixture of 1,3-dimethyl-2-thiobarbituric acid (2.3 g.) and triethylamine (1.7 ml.) in dry benzene (30 ml.). The mixture was refluxed for 12 hours. The mixture was evaporated in vacuo. Diethyl ether (10 ml.) was added to the gummy residue and the mixture was acidified with 1N hydrochloric acid. The mixture was filtered and the solid was washed with water and then ethanol.

Workup

  1. temperatureThe mixture was refluxed for 12 hours
  2. customThe mixture was evaporated in vacuo
  3. additionDiethyl ether (10 ml.) was added to the gummy residue
  4. filtrationThe mixture was filtered
  5. washthe solid was washed with water

Sources & evidence

ORD record
ord-1fc0aa96892f4da8a81efcacb95ef557
Source dataset
uspto-grants-1989_03
Patent number
US04816460

Reaction notes

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