Acetone → 1-(3-chloropropyl)-2,3-dihydro-2,2-dimethyl-4(1H)-quinazolinone

HRID 1156327Notes

Reaction equation

HRID 1156327 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([NH2:10])=[O:9].[CH3:15][C:16](=O)[CH3:17].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:6]2[C:7](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8](=[O:9])[NH:10][C:16]1([CH3:17])[CH3:15]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 196983462-[(3-Chloropropyl)amino]benzamide

Product 1

HCID 202789421-(3-chloropropyl)-2,3-dihydro-2,2-dimethyl-4(1H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10 parts of 2-[(3-chloropropyl)amino]benzamide, 16 parts of 2-propanone, 1 part of 4-methylbenzenesulfonic acid and 40 parts of ethanol is stirred and refluxed overnight. The reaction mixture is evaporated and the oily residue is stirred in 2,2'-oxybispropane. The product is filtered off and dried, yielding 10 parts of 1-(3-chloropropyl)-2,3-dihydro-2,2-dimethyl-4(1H)-quinazolinone.

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture is evaporated
  3. stirringthe oily residue is stirred in 2,2'-oxybispropane
  4. filtrationThe product is filtered off
  5. customdried

Sources & evidence

ORD record
ord-59a11f4c179047c7bc16dd0bd9ffb495
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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