Water → HCID 20080846, compound

HRID 1653850Notes

Reaction equation

HRID 1653850 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)=[C:5]([CH3:27])[NH:4][C:3]=1[CH3:28].[H-].[Na+].[C:31](Cl)(=[O:33])[CH3:32].O>CN(C=O)C>[C:31]([O:8][C:7]1[C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:24])([F:25])[F:26])=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)=[C:5]([CH3:27])[N:4]=[C:3]([CH3:28])[C:2]=1[Cl:1])(=[O:33])[CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 9887751GW 844520

Product 1

HCID 20080846HCID 20080846, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 3-Chloro-5-(4-(4-trifluoromethoxyphenoxy)phenyl)-2,6-dimethyl pyridin-4(1H)-one (0.41 g) in dry DMF, under nitrogen, was added all at once sodium hydride (0.05 g of a 60% dispersion in mineral oil). After stirring at rt for 30 min acetyl chloride (0.14 ml) was added. The mixture was stirred at rt for a further 2 hr, poured into iced water, extracted with ether, washed with water and satd. aq. sodium bicarbonate and dried over magnesium sulphate. Evaporation gave an oil which was triturated with hexane to give the title compound (0.2 g), m.p. 78°-80°, Nmr δH (CDCl3) 7.3-7.0 (8H, m), 2.68 (3H, s), 2.35 (3H, s), 2.05 (3H, s).

Workup

  1. additionwas added
  2. extractionextracted with ether
  3. washwashed with water
  4. dry with materialaq. sodium bicarbonate and dried over magnesium sulphate
  5. customEvaporation
  6. customgave an oil which
  7. customwas triturated with hexane

Sources & evidence

ORD record
ord-0fefcb58bbd04b69ace9ea9bd7fa20fe
Source dataset
uspto-grants-1995_04
Patent number
US05403934

Reaction notes

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