Thionyl Chloride → 3-(2-chloroethyl)-2-phenylquinazolin-4(3H)-one

HRID 1156345Notes

Reaction equation

HRID 1156345 reaction equation
O[CH2:2][CH2:3][N:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.S(Cl)([Cl:23])=O>ClC(Cl)Cl>[Cl:23][CH2:2][CH2:3][N:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 8545423-(2-Hydroxyethyl)-2-phenyl-quinazolin-4-one

Product 1

HCID 27720803-(2-chloroethyl)-2-phenylquinazolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 15 parts of 3-(2-hydroxyethyl)-2-phenyl-4(3H)-quinazolineone and 375 parts of trichloromethane are added dropwise 24 parts of thionyl chloride at room temperature. Upon completion, stirring is continued for 2 hours at reflux. The reaction mixture is evaporated. Water is added to the residue and the whole is neutralized with a sodium hydrogen carbonate solution. The product is extracted with trichloromethane. The extract is washed with water, dried, filtered and evaporated. The residue is crystallized from a mixture of 2,2'-oxybispropane and petroleumether. The product is filtered off and dried, yielding 11.6 parts of 3-(2-chloroethyl)-2-phenyl-4(3H)-quinazolinone.

Workup

  1. temperatureat reflux
  2. customThe reaction mixture is evaporated
  3. additionWater is added to the residue
  4. extractionThe product is extracted with trichloromethane
  5. washThe extract is washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is crystallized from a mixture of 2,2'-oxybispropane and petroleumether
  10. filtrationThe product is filtered off
  11. customdried

Sources & evidence

ORD record
ord-6de35fc962be44e6a21e2ac5d8b0013b
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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