Sodium ethoxide → HCID 21106514, compound

HRID 1783691Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23].ClC1C=C(C(F)(F)F)C=CC=1NN.[O-]CC.[Na+]>CCO>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[N:12]1[NH:13][C:14](=[O:23])[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]1=[O:22]

Participants

Conditions

Temperature: 85 °C

Procedure

1.74 g 2-(2-Chloro-4-trifluoromethyl-phenylamino)-isoindole-1,3-dione (prepared from 2-chloro-4-trifluoromethyl-phenylhydrazine analogously to method A) in 80 ml dry EtOH were treated with 347 mg sodium ethoxide and the mixture was stirred at 85° C. for 2 hrs. After cooling, the mixture was evaporated and dissolved in water. Precipitate was filtered off and washed several times with water. The combined filtrates was acidified by addition of conc. HCl whereupon the product precipitated. It was isolated by filtration and purified by chromatography on silica eluting with a gradient from heptane/EtOAc (50:50) to pure EtOAc. Yield 250 mg (40%)

Workup

temperatureAfter cooling
customthe mixture was evaporated
dissolutiondissolved in water
filtrationPrecipitate was filtered off
washwashed several times with water
additionThe combined filtrates was acidified by addition of conc. HCl whereupon the product
customprecipitated
customIt was isolated by filtration
custompurified by chromatography on silica eluting with a gradient from heptane/EtOAc (50:50) to pure EtOAc

Sources & evidence

ORD record: ord-f71da353e1b5486fb7a994ac7a0fd029
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501410B2

Reaction notes

Loading…