Diethyl chlorophosphate → HCID 20080829, compound

HRID 1653852Notes

Reaction equation

HRID 1653852 reaction equation
[Br: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+].[P:31](Cl)([O:36][CH2:37][CH3:38])([O:33][CH2:34][CH3:35])=[O:32]>CN(C=O)C>[P:31]([O:36][CH2:37][CH3:38])([O:33][CH2:34][CH3:35])([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[Br:1])=[O:32]

Participants

5

Reactant 3

HCID 13139Diethyl chlorophosphateHCID 24758Sodium hydrideHCID 20080827HCID 20080827, compound

Product 1

HCID 20080829HCID 20080829, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-Bromo-5-(4-(4-trifluoromethoxyphenoxy)phenyl)-2,6-dimethyl pyridin-4(1H)-one (4.44 g) in dry DMF (30 ml) under nitrogen was added sodium hydride (0.39 g of a 60% dispersion in mineral oil). After stirring at rt for 30 min diethyl chlorophosphate (2.1 ml) was added dropwise. The mixture was stirred at rt for 48 hr then filtered. The filtrate was diluted with toluene (200 ml), washed with 2M sodium carbonate, dried over magnesium sulphate and concentrated in vacuo. The residue was chromatographed on silica, eluting with 1:4 ethyl acetate:dichloromethane to afford the title compound (1.22 g), m.p. 80°-81°, NMR δH (CDCl3) 7.35-7.0 (8H, m), 4-3.8 (4H, m), 2.7 (3H, s), 2.25 (3H, s), 1.25-1.15 (6H, 2×t).

Workup

  1. additionwas added dropwise
  2. filtrationthen filtered
  3. additionThe filtrate was diluted with toluene (200 ml)
  4. washwashed with 2M sodium carbonate
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica
  8. washeluting with 1:4 ethyl acetate

Sources & evidence

ORD record
ord-682087d62c744a62bc04cf4b55298d00
Source dataset
uspto-grants-1995_04
Patent number
US05403934

Reaction notes

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