Methanol → HCID 178488507, compound

HRID 1531824Notes

Reaction equation

HRID 1531824 reaction equation
COC(=O)[C:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)=[CH:5]N(C)C.[CH3:18][NH:19][C:20](=[O:28])[CH2:21][C:22]1[S:23][CH:24]=[C:25]([CH3:27])[N:26]=1.[CH3:29][OH:30].[H-].[Na+]>CN(C)C=O>[OH:30][C:29]1[N:19]([CH3:18])[C:20](=[O:28])[C:21]([C:22]2[S:23][CH:24]=[C:25]([CH3:27])[N:26]=2)=[CH:5][C:4]=1[C:9]1[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 10899117HCID 10899117, compoundHCID 53889968HCID 53889968, compound

Product 1

HCID 178488507HCID 178488507, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Methyl-3-dimethylamino-2-(4-methoxyphenyl)propenoate (1.6 g), N-methyl-2-(4-methylthiazol-2-yl)acetamide (1 g) and methanol (0.28 cm3) were dissolved in N,N-dimethylformamide (30 cm3) and cooled to 0° C. under N2. Sodium hydride (60% suspension in oil, 0.28 g) was added and the mixture heated at 80° C. for 18 h. The mixture was cooled, partitioned between ethyl acetate (200 cm3) and water (200 cm3). The aqueous layer was acidified with 2N HCl and extracted with ethyl acetate (3×100 cm3) which was dried (MgSO4) and evaporated. The crude solid was recrystallised from ethyl acetate/ether to yield pure 6-hydroxy-5-(4-methoxyphenyl)-1-methyl-3-(4-methylthiazol-2-yl)-1H-pyridin-2-one (0.3 g). δH (250 MHz; CDCl3); 2.37 (3H, s), 3.48 (3H, s), 3.83 (3H, s), 6.37 (1H, s), 6.92 (2H, d, J 8.7 Hz), 7.33 (1H, s) and 7.53 (2H, d, J 8.7 Hz); m/z (ESP+) 329 (MH+).

Workup

  1. temperaturethe mixture heated at 80° C. for 18 h
  2. temperatureThe mixture was cooled
  3. custompartitioned between ethyl acetate (200 cm3) and water (200 cm3)
  4. extractionextracted with ethyl acetate (3×100 cm3) which
  5. dry with materialwas dried (MgSO4)
  6. customevaporated
  7. customThe crude solid was recrystallised from ethyl acetate/ether

Sources & evidence

ORD record
ord-2f3b0d72926d4eea99e1b1d84db29d11
Source dataset
uspto-grants-2001_03
Patent number
US06200982B1

Reaction notes

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