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

HRID 1248214Notes

Reaction equation

HRID 1248214 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([NH2:13])=[O:12])C=CC=1.[CH3:18][C:19](=O)[CH3:20].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[Cl:1][CH2:2][CH2:3][CH2:4][N:8]1[C:9]2[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:11](=[O:12])[NH:13][C:19]1([CH3:20])[CH3:18]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 9019312-((3-Chlorophenyl)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-chlorophenyl)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-ec2d18965ec741668cb8fd0561de7ccf
Source dataset
uspto-grants-1985_06
Patent number
US04522945

Reaction notes

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