Ethylenediamine → HCID 86737344, compound

HRID 225012Notes

Reaction equation

HRID 225012 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[C:18]([O:26][O:27][CH:28]([CH2:33][CH2:34][CH2:35][CH3:36])[CH:29](Br)[CH2:30][CH3:31])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH3:37][N:38](C)C=O.C(N)CN>O>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[C:18]([O:26][O:27][CH:28]([CH2:33][CH2:34][CH2:35][CH3:36])[CH:29]([C:37]#[N:38])[CH2:30][CH3:31])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6228DimethylformamideHCID 86737346HCID 86737346, compound

Product 1

HCID 86737344HCID 86737344, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.75 g (5.10-3 moles) of p-pentyl biphenyl-3-bromo-4-octyloxy benzoate and 0.6 g (6.7.10-3 moles) of cuprous cyanide are introduced into 10 ml of dimethyl formamide. After system had been heated under reflux for 6 hours, it is cooled and poured into a mixture of 60 ml of deionized water and 5.5 ml of ethylene diamine. The solution is stirred and then extracted with ether. 2.3 g of crude product are obtained and then purified chromatographically on a column of silica, followed by recrystallization in ethanol. 1.8 g of pure product are obtained.

Workup

  1. temperatureAfter system had been heated
  2. temperatureunder reflux for 6 hours
  3. temperatureit is cooled
  4. extractionextracted with ether
  5. custom2.3 g of crude product are obtained
  6. custompurified chromatographically on a column of silica
  7. customfollowed by recrystallization in ethanol

Sources & evidence

ORD record
ord-c15d2042b47f494f97dceb17bb697109
Source dataset
uspto-grants-1980_11
Patent number
US04235736

Reaction notes

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