Dimethylformamide → HCID 20571554, compound

HRID 1577059Notes

Reaction equation

HRID 1577059 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH2:11][CH3:12])[CH:6]=[CH:5][C:4]=1[O:13][C:14](=[O:30])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:17](Br)[CH:16]=1)#[N:2].[CH3:31][N:32](C)C=O>Cl.O>[C:1]([C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH2:11][CH3:12])[CH:6]=[CH:5][C:4]=1[O:13][C:14](=[O:30])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:17]([C:31]#[N:32])[CH:16]=1)#[N:2]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 20571559HCID 20571559, compound

Product 1

HCID 20571554HCID 20571554, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

9.9 g (0.021 mol) of the (2'-cyano-4'-n-butylphenyl)-3-bromo-4-n-heptyloxybenzoate prepared in Step VI and 4 g of cuprous cyanide were added to 80 ml of N,N-dimethylformamide. The suspension was gently refluxed for four hours. The reaction mixture was cooled to room temperature, poured into a solution of 14.5 g ferric chloride hexahydrate dissolved in a mixed solution of 3.6 ml of concentrated hydrochloric acid and 22 ml of water, and was stirred with heating at 65° C. for 30 minutes in order to decompose any complexes. An organic layer was extracted from the suspension with toluene, was cleaned and was dehydrated. The toluene was distilled off. The residue was recrystallized in ethanol to yield 3.4 g of purified (2'-cyano-4'-n-butylphenyl)-3-cyano-4-n-heptyloxybenzoate. The yield was calculated to be 39.1%.

Workup

  1. temperatureThe suspension was gently refluxed for four hours
  2. temperaturewith heating at 65° C. for 30 minutes in order
  3. extractionAn organic layer was extracted from the suspension with toluene
  4. distillationThe toluene was distilled off
  5. customThe residue was recrystallized in ethanol

Sources & evidence

ORD record
ord-55b16ab2efbc4293be612469a2c1cd4c
Source dataset
uspto-grants-1981_09
Patent number
US04287085

Reaction notes

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