Dimethylformamide → HCID 86583795, compound

HRID 1978857Notes

Reaction equation

HRID 1978857 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[NH:15][C:14]2=O)=[CH:9][C:8]=1[CH:25]=[C:26]([Cl:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28].CN(C)C=O>ClCCl>[Cl:3][C:14]1[N:13]([C:10]2[CH:11]=[CH:12][C:7]([Cl:6])=[C:8]([CH:25]=[C:26]([Cl:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:9]=2)[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:21])([F:23])[F:22])[N:15]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 86756860HCID 86756860, compound

Product 1

HCID 86583795HCID 86583795, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

13.8 ml of phosphoryl chloride were added dropwise to 12.6 g of 3-[4-chloro-3-(2-chloro-2-ethoxycarbonylethenyl)-phenyl]-2,4-dioxo-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine, and stirring was carried out for 2 hours at room temperature. Thereafter, 2.1 ml of dimethylformamide were added and stirring was continued for 15 hours at 110-115° C. The reaction mixture was evaporated down under reduced pressure, the residue was added to 150 ml of ice water and the mixture was extracted with twice 100 ml of dichloromethane. The combined organic phases were washed with water, 10% strength sodium bicarbonate and again with water, dried over sodium sulfate and evaporated down. The oil obtained was subjected to flash chromatography (dichloromethane), and the crystalline solid obtained therefrom was stirred with petroleum ether, removed, washed with a little petroleum ether and dried.

Workup

  1. stirringstirring
  2. waitwas continued for 15 hours at 110-115° C
  3. customThe reaction mixture was evaporated down under reduced pressure
  4. additionthe residue was added to 150 ml of ice water
  5. extractionthe mixture was extracted with twice 100 ml of dichloromethane
  6. washThe combined organic phases were washed with water, 10% strength sodium bicarbonate and again with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated down
  9. customThe oil obtained
  10. customthe crystalline solid obtained
  11. customremoved
  12. washwashed with a little petroleum ether
  13. customdried

Sources & evidence

ORD record
ord-c15d7bffa89b4e519c4565a89bc6d978
Source dataset
uspto-grants-2001_05
Patent number
US06239074B1

Reaction notes

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