Thionyl Chloride → HCID 21183965, compound

HRID 1938564Notes

Reaction equation

HRID 1938564 reaction equation
S(Cl)(Cl)=O.[C:5]([CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:23]=[C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]4[O:32][CH2:33][O:34][C:28]=4[CH:27]=3)[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Cl:35])[CH:20]=3)[N:15]=2)[CH2:10][CH2:9]1)(=O)[NH2:6]>C(#N)C>[C:5]([CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:23]=[C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]4[O:32][CH2:33][O:34][C:28]=4[CH:27]=3)[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Cl:35])[CH:20]=3)[N:15]=2)[CH2:10][CH2:9]1)#[N:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21183891HCID 21183891, compound

Product 1

HCID 21183965HCID 21183965, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

75 ml of thionyl chloride and 150 ml of acetonitrile were added to 3.8 g (0.0086 mol) of 2-(4-carbamoylpiperidino)-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline. The mixture thus obtained was heated under reflux for one hour. The reaction mixture was distilled under a reduced pressure to remove the solvent. A saturated aqueous solution of sodium hydrogencarbonate and triethylamine were added to the residue and the resultant mixture was reacted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, filtered and distilled under a reduced pressure to remove the solvent. The obtained residue was purified by a silica gel column chromatography (ethyl acetate-n-hexane) and recrystallized from chloroform-n-hexane to give 3.1 g of the title compound.

Workup

  1. customThe mixture thus obtained
  2. temperaturewas heated
  3. temperatureunder reflux for one hour
  4. distillationThe reaction mixture was distilled under a reduced pressure
  5. customto remove the solvent
  6. additionA saturated aqueous solution of sodium hydrogencarbonate and triethylamine were added to the residue
  7. customthe resultant mixture was reacted with ethyl acetate
  8. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. distillationdistilled under a reduced pressure
  12. customto remove the solvent
  13. customThe obtained residue was purified by a silica gel column chromatography (ethyl acetate-n-hexane)
  14. customrecrystallized from chloroform-n-hexane

Sources & evidence

ORD record
ord-c460b2e085b942e4a7239b9313292f77
Source dataset
uspto-grants-1997_12
Patent number
US05693652

Reaction notes

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