Sodium ethoxide → HCID 21106514, compound

HRID 1765377Notes

Reaction equation

HRID 1765377 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+]>C(O)C>[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

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 2736687[2-Chloro-4-(trifluoromethyl)phenyl]hydrazineHCID 21106515HCID 21106515, compound

Product 1

HCID 21106514HCID 21106514, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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 ethanol 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/ethyl acetate (50:50) to pure ethyl acetate. Yield 250 mg (14%)

Workup

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

Sources & evidence

ORD record
ord-9d3716f79cfa46869a2d5370f432b6eb
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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