Dimethylformamide → 3-[3-(2-Bromo-2-chlorocarbonylethenyl)-4-chlorophenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

HRID 1978863Notes

Reaction equation

HRID 1978863 reaction equation
S(Cl)([Cl:3])=O.[Br:5][C:6]([C:28]([OH:30])=O)=[CH:7][C:8]1[CH:9]=[C:10]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:26])[C:16]2=[O:27])[CH:11]=[CH:12][C:13]=1[Cl:14].CN(C)C=O>C1(C)C=CC=CC=1>[Br:5][C:6]([C:28]([Cl:3])=[O:30])=[CH:7][C:8]1[CH:9]=[C:10]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:23])[F:24])[N:17]([CH3:26])[C:16]2=[O:27])[CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 865837973-[3-(2-Bromo-2-carboxyethenyl)-4-chlorophenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

Product 1

HCID 865837993-[3-(2-Bromo-2-chlorocarbonylethenyl)-4-chlorophenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.6 g of thionyl chloride were added to a solution of 4.5 g of 3-[3-(2-bromo-2-carboxyethenyl)-4-chlorophenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine and 0.1 ml of dimethylformamide in 100 ml of toluene. The reaction mixture was heated slowly to the reflux temperature, stirred under reflux for 5 hours and evaporated down, and the residue was dried under greatly reduced pressure.

Workup

  1. temperatureThe reaction mixture was heated slowly to the reflux temperature
  2. temperatureunder reflux for 5 hours
  3. customevaporated down
  4. customthe residue was dried under greatly reduced pressure

Sources & evidence

ORD record
ord-07bf9b999a46485d88912f25c556707d
Source dataset
uspto-grants-2001_05
Patent number
US06239074B1

Reaction notes

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