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

HRID 1596278Notes

Reaction equation

HRID 1596278 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 176.1%

Reagents, catalysts & solvents 1

HCID 244Benzyl AlcoholSolvent

Procedure

Sodium metal (2.2 g, 95 mmol) was added carefully to benzyl alcohol (50 ml) at ambient temperature. The mixture was stirred for 30 minutes at ambient temperature and then heated at 80° C. for 1 hour. The mixture was allowed to cool to 40° C. and 7-fluoro-3,4-dihydroquinazolin-4-one (3.9 g, 24 mmol), (prepared as described for the starting material in Example 1), was added. The reaction mixture was then stirred and heated at 130° C. for 4 hours and left to cool to ambient temperature overnight. The mixture was quenched with water, the resulting precipitate wvas triturated by the addition of ether (150 ml), collected by filtration and dried for 4 hours at 60° C. under high vacuum to give 7-benzyloxy-3,4-dihydroquinazolin-4-one (5.33 g, 89%).

Workup

  1. temperatureheated at 80° C. for 1 hour
  2. temperatureto cool to 40° C.
  3. additionwas added
  4. stirringThe reaction mixture was then stirred
  5. temperatureheated at 130° C. for 4 hours
  6. waitleft
  7. temperatureto cool to ambient temperature overnight
  8. customThe mixture was quenched with water
  9. customthe resulting precipitate wvas triturated by the addition of ether (150 ml)
  10. filtrationcollected by filtration
  11. customdried for 4 hours at 60° C. under high vacuum

Sources & evidence

ORD record
ord-d76ce88946f04b1399e765aa5f1682a1
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

Loading…