Benzyl Alcohol → HCID 178518222, compound

HRID 639984Notes

Reaction equation

HRID 639984 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[F:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1F)[NH:18][CH:17]=[N:16][C:15]2=[O:23].O>CN(C)C=O>[CH2:1]([O:8][C:21]1[CH:20]=[C:19]2[C:14]([C:15](=[O:23])[N:16]=[CH:17][NH:18]2)=[CH:13][C:12]=1[F:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 178518220HCID 178518220, compound

Product 1

HCID 178518222HCID 178518222, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Benzyl alcohol (4.27 g, 39.5 mmol) was added dropwise to a stirred suspension of sodium hydride (1.6 g of a 60% dispersion in mineral oil, 40.0 mmol) in dimethylformamide (50 ml) at 0° C. The reaction was stirred at 0° C. for 1 hour before addition of 6,7-difluoroquinazolin-4(1H)-one (3.60 g, 19.8 mmol) whereupon the reaction was heated to 60° C. for 2 hours. The reaction was cooled to ambient temperature, poured into water (200 ml) and the resultant solid collected by suction filtration. Drying of the solid in vacuo yielded 7-(benzyloxy)-6-fluoroquinazolin-4(1H)-one (4.45 g, 83% yield) as a pale brown solid:

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. filtrationthe resultant solid collected by suction filtration
  3. customDrying of the solid in vacuo

Sources & evidence

ORD record
ord-c1ab1ef8b04e4f77b608df0a656688c6
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

Loading…