Methanol → HCID 22050484, compound

HRID 1867014Notes

Reaction equation

HRID 1867014 reaction equation
[CH2:1]([N:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:23][N:24]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:25](Cl)=[O:26].CO>C(#N)C.ClCCl>[CH3:23][N:24]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:25](=[O:26])[O:14][C:11]1[CH:12]=[CH:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9](=[O:15])[CH:10]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 54724181HCID 54724181, compound

Product 1

HCID 22050484HCID 22050484, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a chilled solution of 1-benzyl-4-hydroxypyridin-2(1H)-one (0.375 g, 1.86 mmol) in anhydrous acetonitrile (10 mL) was added triethylamine (0.206 g, 2.04 mmol) followed by N-methyl-N-phenylcarbamoyl chloride (0.379 g, 2.24 mmol). The reaction mixture was stirred under nitrogen atmosphere at 0° C. for 30 minutes then at room temperature for 1 hour. The reaction was monitored by TLC (5% methanol in dichloromethane). The solvent was removed under reduced pressure and the residue was washed with 10% citric acid and extracted with ethyl acetate. The organic extracts were combined, washed with water and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to afford a yellow syrup. The residue was purified by flash chromatography (silica gel) using 5% MeOH in CH2Cl2 to give the desired product (0.3829, 61%) as a white semisolid. 1H-NMR (d6-DMSO, 400 MHz) δ7.8 (d, 1H, J=7.2 Hz), 7.39 (m, 10H), 6.19 (s, 2H), 5.03 (s, 2H), 3.29 (s, 3H); ES-HRMS m/z 335.1396 (M+H calculated for C20H19N2O3 requires 335.1418).

Workup

  1. waitat room temperature for 1 hour
  2. customThe solvent was removed under reduced pressure
  3. washthe residue was washed with 10% citric acid
  4. extractionextracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over anhydrous Na2SO4
  7. customThe solvent was removed under reduced pressure
  8. customto afford a yellow syrup
  9. customThe residue was purified by flash chromatography (silica gel)

Sources & evidence

ORD record
ord-67281b163aee4176a4908b5b03d4c314
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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