Hydrochloric Acid → HCID 11026766, compound

HRID 353149Notes

Reaction equation

HRID 353149 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[CH2:20][CH2:19][N:18]([C:21](=S)[NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]3[O:30][CH2:31][O:32][C:26]=3[CH:25]=2)[CH2:17][CH2:16]1.[OH-].[Na+].OO.S([O-])([O-])(=[O:40])=S.[Na+].[Na+].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[CH2:20][CH2:19][N:18]([C:21]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]3[O:30][CH2:31][O:32][C:26]=3[CH:25]=2)=[O:40])[CH2:17][CH2:16]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 9890746HCID 9890746, compound

Product 1

HCID 11026766HCID 11026766, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 10 ml of ethanol was suspended 152.7 mg (0.33 mmol) of 4-(6,7-dimethoxy-4-quinazolinyl)-N-(3,4-methylenedioxybenzyl)-1-piperazinethiocarboxamide obtained in Example 208, and 1 ml of a 10 N aqueous solution of sodium hydroxide and 1 ml of 30% aqueous hydrogen peroxide were added thereto, followed by overnight stirring. After addition of an aqueous solution of sodium thiosulfate, 4 N hydrochloric acid was added to the reaction mixture for neutralization. The resulting mixture was extracted with dichloromethane, and the organic layer was washed with water and dried over sodium sulfate. After the solvent was evaporated, the residue was purified by silica gel chromatography to give the desired compound as colorless crystals.

Workup

  1. additionwere added
  2. additionwas added to the reaction mixture for neutralization
  3. extractionThe resulting mixture was extracted with dichloromethane
  4. washthe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. customAfter the solvent was evaporated
  7. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-09b65c9969f44d2487522c2a5ea710f1
Source dataset
uspto-grants-2004_06
Patent number
US06750218B2

Reaction notes

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