2,2-Dimethylsuccinic anhydride → 3-carboxy-3-methyl-butanoic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide

HRID 2380671Notes

Reaction equation

HRID 2380671 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].[CH3:21][C:22]1([CH3:29])[CH2:27][C:26](=[O:28])[O:25][C:23]1=[O:24]>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:26](=[O:28])[CH2:27][C:22]([C:23]([OH:25])=[O:24])([CH3:29])[CH3:21])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 870672,2-Dimethylsuccinic anhydrideHCID 153383534'-Butylaminomethyl-2-cyanobiphenyl

Product 1

HCID 540530333-carboxy-3-methyl-butanoic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3.6 g (13.5 mmol) of N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amine and 1.75 g (13.5 mmol) of 2,2-dimethylsuccinic acid anhydride in 50 ml of dioxane is heated under reflux for 5 hours. Concentration of the reaction mixture by evaporation yields crude 3-carboxy-3-methyl-butanoic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide that melts at from 125° to 131° and is further used in crude form.

Workup

  1. temperatureunder reflux for 5 hours
  2. customConcentration of the reaction mixture by evaporation

Sources & evidence

ORD record
ord-f9115d28e14040f983b352faf8a5f312
Source dataset
uspto-grants-1994_11
Patent number
US05369110

Reaction notes

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