Thionyl Chloride → HCID 13476546, compound

HRID 1156341Notes

Reaction equation

HRID 1156341 reaction equation
O[CH2:2][CH2:3][N:4]1[CH:13]([CH3:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]1=[O:15].S(Cl)([Cl:18])=O>ClC(Cl)Cl>[Cl:18][CH2:2][CH2:3][N:4]1[CH:13]([CH3:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]1=[O:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20278969HCID 20278969, compound

Product 1

HCID 13476546HCID 13476546, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 8 parts of 3,4-dihydro-3-(2-hydroxyethyl)-4-methyl-2(1H)-quinazolinone, 8 parts of thionyl chloride and 90 parts of trichloromethane is stirred and refluxed for 1.50 hours. The reaction mixture is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is stirred in 2,2'-oxybispropane. The product is filtered off and dried, yielding 6.6 parts of 3-(2-chloroethyl)-3,4-dihydro-4-methyl-2(1H)-quinazolinone; mp. 126.4° C.

Workup

  1. temperaturerefluxed for 1.50 hours
  2. customThe reaction mixture is evaporated
  3. customThe residue is purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  5. customThe pure fractions are collected
  6. customthe eluent is evaporated
  7. stirringThe residue is stirred in 2,2'-oxybispropane
  8. filtrationThe product is filtered off
  9. customdried

Sources & evidence

ORD record
ord-213172111be84b469fc21e08b4233232
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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