m-Chloroperbenzoic acid → HCID 21529377, compound

HRID 1658439Notes

Reaction equation

HRID 1658439 reaction equation
[CH2:1]([N:4]1[C:10]2[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=2[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])=[N:7][CH2:6][C:5]1=[O:23])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:32])C=1>C(Cl)(Cl)Cl>[CH2:1]([N:4]1[C:10]2[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=2[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])=[N+:7]([O-:32])[CH2:6][C:5]1=[O:23])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21529372HCID 21529372, compound

Product 1

HCID 21529377HCID 21529377, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6.4 g of 1-allyl-7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one in 50 ml of chloroform are treated with 7 g of m-chloroperbenzoic acid and stirred for 16 hours at room temperature. Then the chloroform solution is washed with 1 N sodium bisulfite solution, with 2 N sodium hydroxide and with water. The organic phase is dried over calcium chloride, filtered and concentrated. The residue is recrystallized from ethanol and there is obtained 1-allyl-7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one 4-oxide of melting point 183°C.

Workup

  1. washThen the chloroform solution is washed with 1 N sodium bisulfite solution, with 2 N sodium hydroxide and with water
  2. dry with materialThe organic phase is dried over calcium chloride
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-76bad48aa81b4aec91282f0f942c17a1
Source dataset
uspto-grants-1976_06
Patent number
US03963777

Reaction notes

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