Phosphorus oxychloride → HCID 18315854, compound

HRID 1531825Notes

Reaction equation

HRID 1531825 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 reflux 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, J 8.7 Hz), 7.01 (1H, s) 7.33 (2H, d, J 8.7 Hz) and 8.60 (1H, s).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.5 h
  3. customThe excess reagent was then removed by evaporation
  4. customthe residue partitioned between ethyl acetate (100 cm3) and saturated sodium bicarbonate solution (50 cm3)
  5. washThe aqueous layer was washed with ethyl acetate (2×100 cm3)
  6. dry with materialthe combined organic phase dried (MgSO4)
  7. customevaporated
  8. customPurification on silica gel eluting with ethyl acetate-hexane mixtures

Sources & evidence

ORD record
ord-0ac60f1acb9642dab08ba6d6815bef1b
Source dataset
uspto-grants-2001_03
Patent number
US06200982B1

Reaction notes

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