Water → HCID 85865895, compound

HRID 1296700Notes

Reaction equation

HRID 1296700 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([S:16][CH3:17])[N:11]=2)=[CH:4][CH:3]=1.Cl.[NH2:20][OH:21].C([O-])(=O)C.[Na+].O>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:20][OH:21])[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([S:16][CH3:17])[N:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 117474161-(4-Fluorophenyl)-2-[2-(methylsulfanyl)pyrimidin-4-yl]ethan-1-one

Product 1

HCID 85865895HCID 85865895, compoundYield 498.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-2-[2-(methylsulfanyl)pyrimidin-4-yl]ethanone (91.49 g,48 mmol) in acetonitrile (1.8 L) was added hydroxylamine hydrochloride (121 g, 91.7 mol) and sodium acetate (139 g, 1.7 mol). The reaction was stirred for 24 hours before 100 mL of water was added. The reaction was stirred for 24 hours. The mixture was filtered through a glass frit and the filtrate partitioned between dichloromethane and water. The layers were separated and the aqueous phase extracted with dichloromethane (2×500 mL). The organic layers were combined, washed with saturated aqueous sodium bicarbonate (300 mL), washed with brine (300 mL), dried over magnesium sulfate, filtered and concentrated. The residue was recrystalized from dichloromethane and hexanes to yield 66.4 g (69%) of 1-(4-fluorophenyl)-2-[2-(methylsulfanyl)pyrimidin-4-yl]ethanone oxime. 1H NMR (CDCl3): δ 8.75 (m, 1H), 8.42 (d, 1H), 7.75 (dd, 2H), 7.09 (t, 2H), 6.98 (d, 1H), 4.29 (s, 2H), 2.54 (s, 3H). MS m/z 278 (M+1).

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered through a glass frit
  3. customthe filtrate partitioned between dichloromethane and water
  4. customThe layers were separated
  5. extractionthe aqueous phase extracted with dichloromethane (2×500 mL)
  6. washwashed with saturated aqueous sodium bicarbonate (300 mL)
  7. washwashed with brine (300 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was recrystalized from dichloromethane and hexanes

Sources & evidence

ORD record
ord-c0337a7c8ea349229c958f763242885d
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Reaction notes

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