Ethylenediamine → HCID 86737091, compound

HRID 2057688Notes

Reaction equation

HRID 2057688 reaction equation
[C:1]([Cu])#[N:2].CN(C)C=O.[CH2:9]([O:17][C:18]1[CH:41]=[CH:40][C:21]([C:22]([O:24][C:25]2([CH2:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36](Br)=[CH:35][CH:34]=3)[CH:30]=[CH:29][CH:28]=[CH:27][CH2:26]2)=[O:23])=[CH:20][CH:19]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(N)CN>O.C1C=CC=CC=1>[CH2:9]([O:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][C:25]2([CH2:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([C:1]#[N:2])=[CH:35][CH:34]=3)[CH:26]=[CH:27][CH:28]=[CH:29][CH2:30]2)=[O:23])=[CH:40][CH:41]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 3301EthylenediamineHCID 6228DimethylformamideHCID 86737092HCID 86737092, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 86737091HCID 86737091, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

The following are successively charged into an Erlenmeyer flask: 0.24 g (≃0.0027 mole) of CuCN, 1.5 ml of dimethylformamide (DMF) and 1 g (>0.002 mole) of 1-(4'-octyloxybenzoyloxy) phenyl-2-(4-bromophenyl) ethane. The whole is brought to 160° C. fot six hours while stirring briskly. The mixture is then allowed to cool to ambient temperature. It is poured into a solution of 0.7 g of ethylene diamine in 10 ml of water. It is stirred again for an hour. Benzene is poured into the solution in order to dissolve and extract the cyano product. Filtering is carried out on infus orial earth. The liquid is poured off. The aqueous fraction is washed with benzene. The organic fractions are placed together. They are washed with water until neutral. Drying is carried out on anhydrous Na2SO4. The solvent is evaporated, and chromatography is performed on a column with the mixture of 50% benzene and 50% hexane as an eluent. The product obtained is recrystallised in this mixture of solvents. 600 mg of product are obtained. The molar efficiency is 66%.

Workup

  1. additionThe following are successively charged into an Erlenmeyer flask
  2. stirringIt is stirred again for an hour
  3. dissolutionto dissolve
  4. extractionextract the cyano product
  5. filtrationFiltering
  6. additionThe liquid is poured off
  7. washThe aqueous fraction is washed with benzene
  8. washThey are washed with water until neutral
  9. customDrying
  10. customThe solvent is evaporated
  11. additionchromatography is performed on a column with the mixture of 50% benzene and 50% hexane as an eluent
  12. customThe product obtained
  13. customis recrystallised in this mixture of solvents

Sources & evidence

ORD record
ord-325e365fc0bf44aea1b863b4c93b1ecc
Source dataset
uspto-grants-1980_07
Patent number
US04212762

Reaction notes

Loading…