HCID 54254236, compound → 2-Chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]benzaldehyde

HRID 1742004Notes

Reaction equation

HRID 1742004 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[N:12]([CH3:21])[C:11]2=[O:22])=[CH:6][C:3]=1[CH2:4][OH:5].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:18])([F:20])[F:19])[N:12]([CH3:21])[C:11]2=[O:22])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 54254236HCID 54254236, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 212012252-Chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 20.08 g of 2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl] benzyl alcohol in 250 ml dichloromethane is added dropwise in the course of 30 minutes with stirring at room temperature to a suspension of 19.38 g of pyridinium chlorochromate in 250 ml of dichloromethane, and stirring of the reaction mixture is continued for 3 hours at 25°-28° C. The clear solution is decanted, the brown residue is washed with 100 ml of dichloromethane, and the dichloromethane solution is filtered through 150 g of silica gel. The filtrate is concentrated, and the residue is recrystallised from n-hexane/ethyl acetate; m.p.: 168°-169° C.

Workup

  1. customThe clear solution is decanted
  2. washthe brown residue is washed with 100 ml of dichloromethane
  3. filtrationthe dichloromethane solution is filtered through 150 g of silica gel
  4. concentrationThe filtrate is concentrated
  5. customthe residue is recrystallised from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-e774e53f348f48738a5e63ca84583c34
Source dataset
uspto-grants-1994_08
Patent number
US05336663

Reaction notes

Loading…