Water → HCID 18402999, compound

HRID 2270909Notes

Reaction equation

HRID 2270909 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12](N)=[CH:11][C:10]=2[C:16]([F:19])([F:18])[F:17])=[CH:6][C:5]([N:20]2[C:25](=[O:26])[CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[NH:22][C:21]2=[O:31])=[C:4]([F:32])[CH:3]=1.N(OC(C)(C)C)=O.O>CN(C)C=O>[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:16]([F:17])([F:18])[F:19])=[CH:6][C:5]([N:20]2[C:25](=[O:26])[CH:24]=[C:23]([C:27]([F:29])([F:30])[F:28])[NH:22][C:21]2=[O:31])=[C:4]([F:32])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10906Tert-Butyl nitriteHCID 18402937HCID 18402937, compound

Product 1

HCID 18402999HCID 18402999, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-[4-Chloro-2-fluoro-5-(4-amino-2-trifluoromethylphenoxy)phenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (3.0 g) dissolved in anhydrous N,N-dimethylformamide (10 ml) was added to a solution of t-butyl nitrite (1.28 g) in anhydrous N,N-dimethylformamide (40 ml) kept at 60-5° C. under nitrogen. The resulting mixture was stirred for 30 minutes at this temperature. The solution was poured into water and extracted with ethyl acetate: hexane, 1:1, (300 ml). The organic phase was washed with brine and dried over anhydrous sodium sulfate. After removal of the solvent, the residue was chromatographed on silica gel eluting with ethyl acetate:hexane, 1:2. 3-[4-Chloro-2-fluoro-5-(2-trifluoromethylphenoxy)phenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimid-ine-2,4-dione (Intermediate 11-28) was isolated as an amorphous solid (1.64 g).

Workup

  1. customkept at 60-5° C. under nitrogen
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removal of the solvent
  6. customthe residue was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-884d6d43b76f4647987346384791937b
Source dataset
uspto-grants-2001_12
Patent number
US06333296B1

Reaction notes

Loading…