Potassium Cyanide → HCID 15334671, compound

HRID 430923Notes

Reaction equation

HRID 430923 reaction equation
[C-:1]#[N:2].[K+].[F:4][C:5]1[CH:10]=[C:9](F)[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[N:15]1[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:26])[C:16]1=[O:27]>CS(C)=O>[C:1]([C:9]1[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]([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])=[C:5]([F:4])[CH:10]=1)#[N:2]

Participants

4

Reactant 2

HCID 9032Potassium Cyanide2×HCID 18762345HCID 18762345, compound

Product 1

HCID 15334671HCID 15334671, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium cyanide (0.5 g) was added to a solution of 3-[2,4-difluoro-5-nitrophenyl]-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (2.5 g) in 50 ml of anhydrous dimethyl sulfoxide. The reaction mixture was subsequently stirred for 10 hours at room temperature, more potassium cyanide (0.16 g) being added after 5 hours. For working-up, most of the solvent was removed at 80° C. under a high vacuum. The residue was taken up in 150 ml of water, washed three times using in each case 30 ml of water, dried over sodium sulfate and concentrated. Chromatography on silica gel (dichloromethane as eluent) and crystallization using petroleum ether gave 1.2 g of the desired product; m.p.: 155-157° C. The following compounds of Table 3 were prepared in a similar manner:

Workup

  1. customwas removed at 80° C. under a high vacuum
  2. washwashed three times
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customChromatography on silica gel (dichloromethane as eluent) and crystallization

Sources & evidence

ORD record
ord-4468375fd5f24f87b5be880699062b42
Source dataset
uspto-grants-2003_12
Patent number
US06656884B2

Reaction notes

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