m-Chloroperbenzoic acid → HCID 178491621, compound

HRID 1293455Notes

Reaction equation

HRID 1293455 reaction equation
N1C=CC([NH:7][C:8]([C:10]2[C:18]3[C:17]4[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=4[O:15][C:14]=3[C:13]([O:23][CH3:24])=[CH:12][CH:11]=2)=[O:9])=CC=1.ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)(Cl)Cl>[CH3:24][O:23][C:13]1[C:14]2[O:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[C:18]=2[C:10]([C:8]([NH2:7]=[O:33])=[O:9])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10018761HCID 10018761, compound

Product 1

HCID 178491621HCID 178491621, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of N-(pyrid-4-yl)-4-methoxy dibenzo[b,d]furan-1-carboxamide (150 mg, 0.47 mmol) (example 3) and m-chloroperbenzoic acid (50-55%) (406 mg, 2.3 mmol) in chloroform (2.5 ml) was stirred at room temperature for 16 h. Chloroform was evaporated and the resulting solid was washed with saturated sodium bicarbonate solution, water, dried and then purified by column chromatography using 20% acetone-chloroform as the eluent to give 70 mg of N-pyrid-4-yl)-4-methoxy dibenzo[b,d]furan-1-carboxamide-N1-oxide as white solid; nip: 246-251° C.; IR (KBr): 3207, 3116, 3056, 2931, 2840, 2797, 1678, 1626, 1603, 1530, 1485, 1458, 1439, 1391, 1330, 1277, 1214, 1174, 1122, 1099, 1023, 851, 829, 791, 749 cm−1.

Workup

  1. customChloroform was evaporated
  2. washthe resulting solid was washed with saturated sodium bicarbonate solution, water
  3. customdried
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-56504ec78cac4678a1c344ee506e9443
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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