Phenylacetonitrile → Benzamide, 2-hydroxy-3,5-diiodo- (9CI)

HRID 1415586Notes

Reaction equation

HRID 1415586 reaction equation
[OH:1][C:2]1[C:10]([I:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].C1(CC#[N:21])C=CC=CC=1>O1CCOCC1>[OH:1][C:2]1[C:10]([I:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([NH2:21])=[O:5]

Participants

4

Reactant 2

HCID 8794PhenylacetonitrileHCID 30163142-Hydroxy-3,5-diiodobenzoyl chloride

Product 1

HCID 205488Benzamide, 2-hydroxy-3,5-diiodo- (9CI)

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4.9 parts of 2-hydroxy-3,5-diiodobenzoyl chloride and 3.7 parts of 4-amino-2-(trifluoromethyl)-α-[3-trifluoromethyl)phenyl]benzeneacetonitrile in 60 parts of 1,4-dioxane is stirred and refluxed for 10 minutes. The reaction mixture is evaporated. The residue is boiled in methylbenzene for 10 minutes. After cooling to room temperature, the precipitated product is filtered off, yielding N-[4-{α-cyano-α-[3-trifluoromethyl)phenyl]methyl-}3-(trifluoromethyl)phenyl]-2-hydroxy-3,5-diiodobenzamide; mp. 206.3° C.

Workup

  1. temperaturerefluxed for 10 minutes
  2. customThe reaction mixture is evaporated
  3. filtrationthe precipitated product is filtered off

Sources & evidence

ORD record
ord-6d75411197334bdfaa3e2ee63d379c43
Source dataset
uspto-grants-1977_01
Patent number
US04005218

Reaction notes

Loading…