Hydroxyamine hydrochloride → HCID 136401256, compound

HRID 1755995Notes

Reaction equation

HRID 1755995 reaction equation
[C:1]([C:4]1[N:9]=[C:8]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])[CH:7]=[CH:6][N:5]=1)(=O)[CH3:2].Cl.[NH2:17][OH:18].C([O-])(=O)C.[Na+]>C(O)C.O>[C:1](=[N:17][OH:18])([C:4]1[N:9]=[C:8]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])[CH:7]=[CH:6][N:5]=1)[CH3:2]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 19392516HCID 19392516, compound

Product 1

HCID 136401256HCID 136401256, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

2-Acetyl-4-(2,2,2-trifluoroethoxy)-pyrimidine (0.47 g) was dissolved in a mixture of ethanol (10 ml) and water (5 ml) and heated to 40° C. for 1 hour with hydroxylamine hydrochloride (0.16 g) and sodium acetate (0.43 g). The reaction mixture was poured into water and extracted with ethyl acetate (3×50 ml). The combined extracts were dried and concentrated. The residue was washed with hexane to give 2-acetyl-4-(2,2,2-trifluoroethoxy)-pyrimidine oxime (0.35 g, 70% yield) as a white solid, m.p. 179°-181° C.; 1H NMR (270 MHz): δ2.39(3H,s), 4.87(2H,q), 6.88(1H,d), 8.60(1H,d) ppm.

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. customThe combined extracts were dried
  3. concentrationconcentrated
  4. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-4b162cc8c83f410a821c5c298ee69bc6
Source dataset
uspto-grants-1995_08
Patent number
US05439910

Reaction notes

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