Thionyl Chloride → 3-(2-chloroethyl)-1-methyl-2,4(1H,3H)-quinazolinedione

HRID 477674Notes

Reaction equation

HRID 477674 reaction equation
O[CH2:2][CH2:3][N:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:15])[C:5]1=[O:16].S(Cl)([Cl:19])=O>ClC(Cl)Cl>[Cl:19][CH2:2][CH2:3][N:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:15])[C:5]1=[O:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 149898923-(2-hydroxyethyl)-1-methyl-2,4(1H,3H)-quinazolinedione

Product 1

HCID 149898933-(2-chloroethyl)-1-methyl-2,4(1H,3H)-quinazolinedioneYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 4.5 parts of 3-(2-hydroxyethyl)-1-methyl-2,4(1H,3H)-quinazolinedione, 8 parts of thionyl chloride and 75 parts of trichloromethane was stirred and refluxed for 5 hours. The reaction mixture was evaporated, yielding 4.5 parts (95%) of 3-(2-chloroethyl)-1-methyl-2,4(1H,3H)-quinazolinedione as a residue (intermediate 171).

Workup

  1. temperaturerefluxed for 5 hours
  2. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-2b68d0fbcd524debb438329d405ff965
Source dataset
uspto-grants-1989_12
Patent number
US04888426

Reaction notes

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