2-Bromoethanol → 3-(2-Hydroxyethyl)-2-phenyl-quinazolin-4-one

HRID 1248230Notes

Reaction equation

HRID 1248230 reaction equation
[C:1]1([C:7]2[NH:16][C:15](=[O:17])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:21][CH2:22][OH:23]>CN(C)C=O>[OH:23][CH2:22][CH2:21][N:16]1[C:15](=[O:17])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 24758Sodium hydrideHCID 1354004562-Phenyl-4(3H)-Quinazolinone

Product 1

HCID 8545423-(2-Hydroxyethyl)-2-phenyl-quinazolin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 18 parts of 2-phenyl-4(3H)-quinazolinone and 225 parts of N,N-dimethylformamide are added portionwise at room temperature 3.2 parts of sodium hydride dispersion 60% (exothermic reaction: the temperature rises to 34° C.). After the addition is complete, the whole is stirred for 10 minutes whereafter 12.4 parts of 2-bromoethanol are added dropwise (slightly exothermic). Upon completion, stirring is continued first for one hour at room temperature, then for 2 hours at 80° C. and further overnight at room temperature. The reaction mixture is cooled, poured onto water and the solid product is sucked off. It is washed with water and 2,2'-oxybispropane and dried in vacuo at 60° C., yielding 15 parts of 3-(2-hydroxyethyl)-2-phenyl-4(3H)-quinazolinone.

Workup

  1. customexothermic reaction
  2. customrises to 34° C.
  3. additionAfter the addition
  4. additionare added dropwise (slightly exothermic)
  5. waitfor 2 hours at 80° C.
  6. customfurther overnight
  7. customat room temperature
  8. temperatureThe reaction mixture is cooled
  9. additionpoured onto water
  10. washIt is washed with water and 2,2'-oxybispropane
  11. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-fb559d1bbb154e1bb675a85baaaf678a
Source dataset
uspto-grants-1985_06
Patent number
US04522945

Reaction notes

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