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

HRID 2055559Notes

Reaction equation

HRID 2055559 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]I.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:27][CH2:28][CH2:29][CH2:30][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 813631-Chloro-3-iodopropaneHCID 1354087534(1H)-QuinazolinoneHCID 1354950166,7-Dimethoxy-3H-quinazolin-4-one

Product 1

HCID 223266313-(3-chloropropyl)-6,7-dimethoxy-4(3H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(3-chloropropyl)-6,7-dimethoxy-4(3H)-quinazolinone was prepared starting from 6,7-dimethoxy-4-(3H) quinazolinone (1.61 g, 8 mmol). The quinazolinone was combined with 1-chloro-3-iodopropane (1.9 mL, 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 diluted with water. The solid that formed was collected via vacuum filtration, washed with water and dried, 0.70 g (31%); brown solid; m.p. 143° C., MS: 282.8 (M+H)+

Workup

  1. filtrationThe salts were filtered off
  2. additionthe reaction mixture 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-afb8c1027ada46f891d5564791c66a0f
Source dataset
uspto-grants-2008_02
Patent number
US07332506B2

Reaction notes

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