m-Chloroperbenzoic acid → HCID 10473521, compound

HRID 1900663Notes

Reaction equation

HRID 1900663 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]1[O:35][C:34]2[CH:33]=[CH:32][C:16]([CH2:17][NH:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[C:26]([S:29]([CH3:31])=[O: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:35][C:34]2[CH:33]=[CH:32][C:16]([CH2:17][NH:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[C:26]([S:29]([CH3:31])(=[O:9])=[O:30])[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 10405045HCID 10405045, compound

Product 1

HCID 10473521HCID 10473521, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 0.65 g (3.8 mmol) of m-chloroperbenzoic acid in 20 ml of chloroform was dropped into a solution of 1.00 g (2.93 mmol) of the 4-(3,4-methylenedioxybenzyl)amino-6-methylsulfinylquinazoline prepared in Example 137 under stirring at room temperature. The obtained mixture was stirred at room temperature 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) and recrystallized from chloroform/n-hexane to give 0.85 g of the title compound as a yellow crystal.

Workup

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

Sources & evidence

ORD record
ord-32c25ee3ef0443238fc6c88f509ccb15
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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