Benzyl Alcohol → 7-(Benzyloxy)-3,4-dihydroquinazolin-4-one

HRID 1737596Notes

Reaction equation

HRID 1737596 reaction equation
[Na].[CH2:2]([OH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.F[C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:21])[NH:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1.Cl>O>[CH2:2]([O:9][C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:21])[NH:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 5360545SodiumHCID 1353984967-Fluoroquinazolin-4(3H)-one

Product 1

HCID 1357631107-(Benzyloxy)-3,4-dihydroquinazolin-4-oneYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
148 °C

Procedure

Sodium (368 mg, 16 mmol) was added to benzyl alcohol (10 ml, 96 mmol) and the mixture was heated at 148° C. for 30 minutes. 7-Fluoro-3,4-dihydroquinazolin-4-one (656 mg, 4 mmol), (J. Chem. Soc. section B 1967, 449), was added and the mixture maintained at 148° C. for 24 hours. The reaction mixture was allowed to cool, the solution was poured on to water (170 ml) and the aqueous mixture adjusted to pH3 with concentrated hydrochloric acid. The precipitate was collected by filtration, washed with water, ether and dried under vacuum to give 7-benzyloxy-3,4-dihydroquinazolin-4-one (890 mg, 89%) as a white solid. m.p. 267-269° C.

Workup

  1. temperaturethe mixture maintained at 148° C. for 24 hours
  2. temperatureto cool
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water, ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-1c03a266e9f94ca988949eb453a22de4
Source dataset
uspto-grants-1999_10
Patent number
US05962458

Reaction notes

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