m-Chloroperbenzoic acid → HCID 86743675, compound

HRID 329748Notes

Reaction equation

HRID 329748 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:15]([NH:17][CH:18]2[CH:23]3[CH2:24][CH2:25][N:20]([CH2:21][CH2:22]3)[CH2:19]2)=[O:16])[C:5]2[O:10][CH:9]([CH3:11])[C:8](=[O:12])[N:7]([CH3:13])[C:6]=2[CH:14]=1.ClC1C=CC=C(C(OO)=[O:34])C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:15]([NH+:17]([O-:34])[CH:18]2[CH:23]3[CH2:24][CH2:25][N:20]([CH2:21][CH2:22]3)[CH2:19]2)=[O:16])[C:5]2[O:10][CH:9]([CH3:11])[C:8](=[O:12])[N:7]([CH3:13])[C:6]=2[CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14719841HCID 14719841, compound

Product 1

HCID 86743675HCID 86743675, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5.0 g of 6-chloro-3,4-dihydro-2,4-dimethyl-3-oxo-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide in 150 ml of chloroform is added portionwise 3.7 g of metachloroperbenzoic acid under cooling and stirring. After 0.5 hour, ammonia gas is bubbled through the reaction solution under stirring and the precipitate is filtered off. The mother liquor is distilled off under reduced pressure followed by recrystallizing the residue from ethanol-isopropyl ester to give 6-chloro-3,4-dihydro-2,4-dimethyl-3-oxo-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide N-oxide, melting at 188°-190° C. with decomposition.

Workup

  1. temperatureunder cooling
  2. customammonia gas is bubbled through the reaction solution
  3. stirringunder stirring
  4. filtrationthe precipitate is filtered off
  5. distillationThe mother liquor is distilled off under reduced pressure
  6. customby recrystallizing the residue from ethanol-isopropyl ester

Sources & evidence

ORD record
ord-01210948cf0e4fc3b5ef84c7121dfe85
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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