Homophthalic anhydride → 2-carboxy-phenylacetic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide

HRID 2380684Notes

Reaction equation

HRID 2380684 reaction equation
[CH2:1]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]#[N:20])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH3:4].[C:21]1(=[O:32])[O:27][C:25](=[O:26])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]2[CH2:22]1.C(Cl)Cl.CCOCC.CCCCCC>O1CCOCC1>[CH2:1]([N:5]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]#[N:20])=[CH:9][CH:8]=1)[C:21](=[O:32])[CH2:22][C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25]([OH:27])=[O:26])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 12801Homophthalic anhydrideHCID 153383534'-Butylaminomethyl-2-cyanobiphenylHCID 21850893Dichloromethane ether hexane

Product 1

HCID 539424252-carboxy-phenylacetic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The starting material can be prepared, for example, as follows: A solution of 2.64 g of N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amine and 2.43 g of homophthalic acid anhydride in 50 ml of dioxane is heated under reflux for hour. After removal of the solvent, the residue is taken up in 100 ml of ethyl acetate and washed twice with 50 ml of water each time. After customary treatment, the organic phase yields a crude product that yields, from CH2Cl2 /ether/hexane, 2-carboxy-phenylacetic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide, m.p. 137°-139°.

Workup

  1. temperatureunder reflux for hour
  2. customAfter removal of the solvent
  3. washwashed twice with 50 ml of water each time
  4. customAfter customary treatment, the organic phase yields a crude product

Sources & evidence

ORD record
ord-37e2e7bed79a4351a2f556e361619812
Source dataset
uspto-grants-1994_11
Patent number
US05369110

Reaction notes

Loading…