Phosphorus oxychloride → HCID 18315854, compound

HRID 275768Notes

Reaction equation

HRID 275768 reaction equation
O[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([C:10]2[S:11][CH:12]=[C:13]([CH3:15])[N:14]=2)=[CH:4][C:3]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.O=P(Cl)(Cl)[Cl:26]>>[Cl:26][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([C:10]2[S:11][CH:12]=[C:13]([CH3:15])[N:14]=2)=[CH:4][C:3]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178488507HCID 178488507, compound

Product 1

HCID 18315854HCID 18315854, compound

Procedure

6-Hydroxy-5-(4-methoxyphenyl)-1-methyl-3-(4-methylthiazol-2-yl)-1H-pyridin-2-one (0.13 g) was dissolved in freshly distilled POCl3 (5 cm3) under N2 and heated to refiux for 1.5 h. The excess reagent was then removed by evaporation and the residue partitioned between ethyl acetate (100 cm3) and saturated sodium bicarbonate solution (50 cm3). The aqueous layer was washed with ethyl acetate (2×100 cm3) and the combined organic phase dried (MgSO4) and evaporated. Purification on silica gel eluting with ethyl acetate-hexane mixtures afforded 6-chloro-5-(4-methoxyphenyl)-1-methyl-3-(4-methylthiazol-2-yl)-1H-pyridin-2-one as a yellow powder. δH (250 MHz; CDCl3); 2.49 (3H, s), 3.86 (3H, s), 3.93 (3H, s), 6.96 (2H, d, J8.7 Hz), 7.01 (1H, s) 7.33 (2H, d, J8.7 Hz) and 8.60 (1H, s).

Workup

  1. temperatureheated
  2. customThe excess reagent was then removed by evaporation
  3. customthe residue partitioned between ethyl acetate (100 cm3) and saturated sodium bicarbonate solution (50 cm3)
  4. washThe aqueous layer was washed with ethyl acetate (2×100 cm3)
  5. dry with materialthe combined organic phase dried (MgSO4)
  6. customevaporated
  7. customPurification on silica gel eluting with ethyl acetate-hexane mixtures

Sources & evidence

ORD record
ord-e9a60aad6496410aa281c7fdb5f6c3bc
Source dataset
uspto-grants-2002_03
Patent number
US06352994B2

Reaction notes

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