m-Chloroperbenzoic acid → HCID 10405045, compound

HRID 2392868Notes

Reaction equation

HRID 2392868 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]1[O:34][C:33]2[CH:32]=[CH:31][C:16]([CH2:17][NH:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[C:26]([S:29][CH3:30])[CH:27]=4)[N:22]=[CH:21][N:20]=3)=[CH:15][C:14]=2[O:13]1>C(Cl)(Cl)Cl>[CH2:12]1[O:34][C:33]2[CH:32]=[CH:31][C:16]([CH2:17][NH:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[C:26]([S:29]([CH3:30])=[O:9])[CH:27]=4)[N:22]=[CH:21][N:20]=3)=[CH:15][C:14]=2[O:13]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10471556HCID 10471556, compound

Product 1

HCID 10405045HCID 10405045, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 1.20 g (6.95 mmol) of m-chloroperbenzoic acid in 30 ml of chloroform was dropped into a solution of 1.80 g (5.53 mmol) of 4-(3,4-methylenedioxybenzyl)amino-6-methylthioquinazoline in 100 ml of chloroform under cooling with ice and stirring. The obtained mixture was stirred under cooling with ice for several hours, washed with a saturated aqueous solution of sodium hydrogencarbonate, dried over anhydrous magnesium sulfate and filtered. The filtrate was purified by silica gel column chromatography (ethyl acetate/acetone) and recrystallized from chloroform/n-hexane to give 1.51 g of the title compound as a pale-yellow crystal.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe obtained mixture was stirred
  3. temperatureunder cooling with ice for several hours
  4. washwashed with a saturated aqueous solution of sodium hydrogencarbonate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was purified by silica gel column chromatography (ethyl acetate/acetone)
  8. customrecrystallized from chloroform/n-hexane

Sources & evidence

ORD record
ord-cb6f2b7af8c74268b815c61a17de6d27
Source dataset
uspto-grants-1998_09
Patent number
US05801180

Reaction notes

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