Potassium Carbonate → 3-(4-chlorobutyl)-6,7-dimethoxy-4(3H)-quinazolinone

HRID 2055558Notes

Reaction equation

HRID 2055558 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][NH:7][C:6]2=[O:15].C1C=CC2N=CNC(=O)C=2C=1.[Cl:27][CH2:28][CH2:29][CH2:30][CH2:31]I.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:27][CH2:28][CH2:29][CH2:30][CH2:31][N:7]1[C:6](=[O:15])[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 825271-Chloro-4-iodobutaneHCID 1354087534(1H)-QuinazolinoneHCID 1354950166,7-Dimethoxy-3H-quinazolin-4-one

Product 1

HCID 223266333-(4-chlorobutyl)-6,7-dimethoxy-4(3H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(4-chlorobutyl)-6,7-dimethoxy-4(3H)-quinazolinone was prepared starting from 6,7-dimethoxy-4(3H)-quinazolinone (1.65 g, 8 mmol). The quinazolinone was combined with 1-chloro-4-iodobutane (1.08 mL, 8.8 mmol), an excess of potassium carbonate (10 g) and stirred in 30 mL DMF overnight. The salts were filtered off and the reaction mixture was diluted with water. The solid that formed was collected via vacuum filtration, washed with water and dried, 1.55 g (65%); gray solid; m.p. 117° C., MS: 296.8 (M+H)+

Workup

  1. filtrationThe salts were filtered off
  2. additionthe reaction mixture was diluted with water
  3. customThe solid that formed
  4. filtrationwas collected via vacuum filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-51a800458a6c462daf91256d3ddbc6a9
Source dataset
uspto-grants-2008_02
Patent number
US07332506B2

Reaction notes

Loading…