m-Chloroperbenzoic acid → HCID 10612690, compound

HRID 326589Notes

Reaction equation

HRID 326589 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([C:14]1[CH:15]=[CH:16][C:17]2[O:22][C:21]([CH3:24])([CH3:23])[N:20]=[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[C:18]=2[CH:31]=1)#[N:13]>ClCCl>[C:12]([C:14]1[CH:15]=[CH:16][C:17]2[O:22][C:21]([CH3:24])([CH3:23])[N:20]=[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N+:26]=3[O-:9])[C:18]=2[CH:31]=1)#[N:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10611577HCID 10611577, compound

Product 1

HCID 10612690HCID 10612690, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (70% purity, 0.75 g) was added at -20° C. to a solution of 6-cyano-2,2-dimethyl-4-(2-pyridyl)-2H-1,3-benzoxazine (0.40 g) in dichloromethane (10 ml) and the mixture was stirred for 30 hours. The reaction mixture was extracted by addition of an aqueous sodium sulfite solution and ethyl acetate. The organic layer was successively washed with aqueous sodium carbonate and saturated saline solution and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was subjected to column chromatography on silica gel, and it was crystallized from isopropyl ether to obtain 2-(6-cyano-2,2-dimethyl-2H-1,3-benzoxazin-4-yl)pyridine N-oxide (0.09 g) (Compound 20). Likewise, Compounds 21 to 29, 32, 36, 38, 43, 45, 47, 49, 51, 56, 58, 60, 63, 65, 67, 69, 71, 73, 75, 77, 79, 81, 83, 85, 87, 89, 91, 93, 95, 97, 106, 107, 108, 109, 110, 117, 118, 119 and 144 were prepared.

Workup

  1. extractionThe reaction mixture was extracted by addition of an aqueous sodium sulfite solution and ethyl acetate
  2. washThe organic layer was successively washed with aqueous sodium carbonate and saturated saline solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customwas crystallized from isopropyl ether

Sources & evidence

ORD record
ord-33fea7f1b51f419ea3e95f36312a6c6a
Source dataset
uspto-grants-1993_12
Patent number
US05270308

Reaction notes

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