Sodium → 7-(Benzyloxy)-3,4-dihydroquinazolin-4-one

HRID 1386316Notes

Reaction equation

HRID 1386316 reaction equation
[Na].F[C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:13])[NH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1>C(O)C1C=CC=CC=1>[CH2:7]([O:13][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:13])[NH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1)[C:6]1[CH:11]=[CH:12][CH:3]=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 1353984967-Fluoroquinazolin-4(3H)-one

Product 1

HCID 1357631107-(Benzyloxy)-3,4-dihydroquinazolin-4-oneYield 118.4%

Reagents, catalysts & solvents 1

HCID 244Benzyl AlcoholSolvent

Conditions

Temperature
80 °C

Procedure

Sodium metal (4.4 g, 191 mmol) was added to benzyl alcohol (100 ml) at ambient temperature and the mixture stirred for 30 minutes then heated at 80° C. for 1 hour. The mixture was then cooled to 40° C. and 7-fluoro-3,4-dihydroquinazolin-4-one (7.8 g, 47 mmol), was added. The reaction mixture was stirred at 130° C. for 4 hours and allowed to cool to ambient temperature and stirred for 18 hours. The solution was quenched with water (800 ml) and acidified to pH3 with concentrated hydrochloric acid. The resulting precipitate was collected by filtration, washed with water and ether and dried for 4 hours at 60° C. under high vacuum to give 7-benzyloxy-3,4-dihydroquinazolin-4-one (7.02 g, 63%).

Workup

  1. temperatureThe mixture was then cooled to 40° C.
  2. stirringThe reaction mixture was stirred at 130° C. for 4 hours
  3. temperatureto cool to ambient temperature
  4. stirringstirred for 18 hours
  5. customThe solution was quenched with water (800 ml)
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water and ether
  8. customdried for 4 hours at 60° C. under high vacuum

Sources & evidence

ORD record
ord-0a11ee268b544487a8b5f8fcf5e99ee2
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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