Thionyl Chloride → HCID 21183965, compound

HRID 2392907Notes

Reaction equation

HRID 2392907 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 etracted 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. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. distillationdistilled under a reduced pressure
  11. customto remove the solvent
  12. customThe obtained residue was purified by a silica gel column chromatography (ethyl acetate-n-hexane)
  13. customrecrystallized from chloroform-n-hexane

Sources & evidence

ORD record
ord-708a51980f3a4feb873583547ab52fb4
Source dataset
uspto-grants-1998_09
Patent number
US05801180

Reaction notes

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