Sodium Acetate → HCID 19354637, compound

HRID 377558Notes

Reaction equation

HRID 377558 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:29])[C:11]([N:14]2[C:19](=[O:20])[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:17]([CH2:27]Br)[O:16][CH2:15]2)([CH3:13])[CH3:12])[CH:6]=[CH:7][CH:8]=1.[C:32]([O-:35])(=[O:34])[CH3:33].[Na+]>CN(C)C=O.CCOCC>[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:29])[C:11]([N:14]2[C:19](=[O:20])[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:17]([CH2:27][O:35][C:32](=[O:34])[CH3:33])[O:16][CH2:15]2)([CH3:13])[CH3:12])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 19354578HCID 19354578, compound

Product 1

HCID 19354637HCID 19354637, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(3-trifluoromethylphenyl)-2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (1.09 g) and sodium acetate (0.36 g) was heated at 80-90° C. in N,N-dimethylformamide for 3 hours. The cooled solution was diluted with ether, washed with water, dried (magnesium sulphate) and evaporated in vacuo to give N-(3-trifluoromethylphenyl)-2-(6-acetoxymethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (compound 103, 0.81 g) as a white solid, m.p. 76.5-77.5° C.

Workup

  1. washwashed with water
  2. dry with materialdried (magnesium sulphate)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-fdd56f15f92842ae85b5679c4fadb1b8
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

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