m-Chloroperbenzoic acid → HCID 85040066, compound

HRID 2307368Notes

Reaction equation

ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[CH:22]=[C:21]([C:23]#[C:24][CH2:25][N:26]([CH3:28])[CH3:27])[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16]>ClCCl>[Cl:12][C:13]1[CH:22]=[C:21]([C:23](=[O:6])[CH:24]=[CH:25][N:26]([CH3:28])[CH3:27])[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

Conditions

Temperature: -20 °C

Procedure

Gradually, 3-chloroperoxybenzoic acid (10.76 g) was added to a solution of 2-chloro-4-(3-dimethylamino-propyn-1yl)-benzoic acid, methyl -ester (15.07 g in dichloromethane (40 ml), at a rate to maintain the reaction temperature at −20° C. The mixture was stirred for 10-15 minutes. The resulting N-oxide was purified by chromatography on Activity Grade I basic alumina (215 g), eluting with 10% methanol/dichloromethane. The solvent was evaporated in vacuo between 12 to 18° C. The resulting residue was dissolved in methanol (100 ml) and heated at 60-65° C. with stirring for 18 hours. After removing the solvent in vacuo, and the product was purified by column chromatography on silica gel (190 g), eluting with 70% ethyl acetate/hexane. Trituration with diethyl ether containing some hexane afforded the title compound as a solid (5.68 g), m.p. 92-96° C.

Workup

customThe resulting N-oxide was purified by chromatography on Activity Grade I basic alumina (215 g)
washeluting with 10% methanol/dichloromethane
customThe solvent was evaporated in vacuo between 12 to 18° C
dissolutionThe resulting residue was dissolved in methanol (100 ml)
temperatureheated at 60-65° C.
stirringwith stirring for 18 hours
customAfter removing the solvent in vacuo
customthe product was purified by column chromatography on silica gel (190 g)
washeluting with 70% ethyl acetate/hexane

Sources & evidence

ORD record: ord-c2e92a5433c84cd7902453f9944307e9
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06831079B1

Reaction notes

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