Carbon Tetrachloride → 2-[4-[4-(2-Chloroethoxy)benzoyl]benzylthio]-3,5-dimethyl-4(3H)-quinazolinone

HRID 1291377Notes

Reaction equation

HRID 1291377 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:13])[N:4]=[C:3]1[S:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:33])[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31]O)=[CH:25][CH:24]=2)=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:54]>>[Cl:54][CH2:31][CH2:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([C:22]([C:19]2[CH:20]=[CH:21][C:16]([CH2:15][S:14][C:3]3[N:2]([CH3:1])[C:11](=[O:12])[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][C:9]=4[CH3:13])[N:4]=3)=[CH:17][CH:18]=2)=[O:33])=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 189188073,5-dimethyl-2-[4-[4-(2-hydroxyethoxy)benzoyl]benzylthio]-4(3H)-quinazolinone

Product 1

HCID 189188132-[4-[4-(2-Chloroethoxy)benzoyl]benzylthio]-3,5-dimethyl-4(3H)-quinazolinone

Procedure

To a suspension of 3,5-dimethyl-2-[4-[4-(2-hydroxyethoxy)benzoyl]benzylthio]-4(3H)-quinazolinone (651 mg) in carbon tetrachloride (15 ml) was added triphenylphosphine (476 mg) and the mixture was refluxed for 40 hours. This reaction mixture was concentrated and the residue was purified by silica gel column chromatography (dichloromethane) and recrystallized from ethyl acetate to provide the title compound as colorless solid (391 mg).

Workup

  1. temperaturethe mixture was refluxed for 40 hours
  2. concentrationThis reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (dichloromethane)
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-119c7775fccb4d41a18c5e0954021bcf
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…