Ethylenediamine → HCID 86737348, compound

HRID 225013Notes

Reaction equation

HRID 225013 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:19]([O:27][CH:28]([CH2:33][CH2:34][CH3:35])[CH:29](Br)[CH2:30][CH3:31])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH3:36][N:37](C)C=O.C(N)CN>O>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:19]([O:27][CH:28]([CH2:33][CH2:34][CH3:35])[CH:29]([C:36]#[N:37])[CH2:30][CH3:31])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6228DimethylformamideHCID 86737350HCID 86737350, compound

Product 1

HCID 86737348HCID 86737348, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.65 g (5.10-3 moles) of p-hexyl biphenyl-3-bromo-4-heptyl benzoate and 0.6 g (6.7×10-3 moles) of cuprous cyanide are introduced into 10 ml of dimethyl formamide. After the solution has been heated under reflux for 7.5 hours, it is cooled and poured into a mixture of 60 ml of deionized water and 5.5 ml of ethylene diamine. After stirring, the solution is extracted with ether. 2.2 g of crude product are obtained, being purified by chromatography on a column of silica, followed by recrystallization from ethanol. 1.6 g of pure product are obtained, corresponding to a yield of 66%.

Workup

  1. temperatureAfter the solution has been heated
  2. temperatureunder reflux for 7.5 hours
  3. temperatureit is cooled
  4. extractionthe solution is extracted with ether
  5. custom2.2 g of crude product are obtained
  6. custombeing purified by chromatography on a column of silica
  7. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-67d966dc96064bf7bbd7f6adccd09857
Source dataset
uspto-grants-1980_11
Patent number
US04235736

Reaction notes

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