Ethylenediamine → HCID 22105592, compound

HRID 1455980Notes

Reaction equation

HRID 1455980 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][C:15]=2[O:21][C:22](=O)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:11][CH3:12])=[CH:6][CH:5]=1.C(N)[CH2:32][NH2:33].ClCCl>CN(C)C=O.O>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:32]#[N:33])=[CH:16][C:15]=2[O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:11][CH3:12])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 6344DichloromethaneHCID 22105659HCID 22105659, compound

Product 1

HCID 22105592HCID 22105592, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of methyl-4-[N-(2-benzoyloxy-4-bromobenzyl)-N-ethylamino]benzoate (5.64 g) and cuprous cyanide (1.28 g) in N,N-dimethylformamide (100 ml) was stirred and heated at 140° C. for 10 hours in an oil bath. The mixture was allowed to cool and was poured into a solution of ethylenediamine (10 ml) in water (240 ml). The resulting mixture was stirred for 30 minutes and then extracted three times with EtoAc (50 ml each time). The oil obtained on removal of the solvent was subjected to chromatography on silica eluting with dichloromethane to give methyl-4-[N-(2-benzyloxy-4-cyanobenzyl)-N-ethylamino]benzoate, yield 3.9 g.

Workup

  1. temperatureto cool
  2. stirringThe resulting mixture was stirred for 30 minutes
  3. extractionextracted three times with EtoAc (50 ml each time)
  4. customThe oil obtained on removal of the solvent

Sources & evidence

ORD record
ord-669fb36e33cf4847a640202fdc2b316d
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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