Ethylenediamine → HCID 12813635, compound

HRID 1603891Notes

Reaction equation

HRID 1603891 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][OH:11])=[CH:7][C:6]=2[CH:12]=1.[Cu][C:14]#[N:15].CN1CCCC1=O.C(N)CN>O>[OH:11][CH2:10][C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([C:14]#[N:15])=[CH:12][C:6]=2[CH:7]=1

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 13387N-methyl-2-pyrrolidoneHCID 2795537(5-Bromo-1-benzofuran-2-yl)methanolHCID 178418546HCID 178418546, compound

Product 1

HCID 12813635HCID 12813635, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

A solution of 5-bromo-2-benzofuranylmethanol (1.19 g, 5.24 mmol), copper (I) cyanide (0.470 g, 5.25 mmol) and N-methylpyrrolidinone (15 ml) was left under stirring at 200° C. for 3.5 h, then was poured onto a solution of ethylenediamine (6 g) in water (80 ml) and extracted with ethyl acetate (3×75 ml). The organic phase was dried and the solvents were evaporated off under reduced pressure. The resulting crude was purified by chromatography through a silica gel column, eluting with n-hexane:ethyl acetate mixtures of increasing polarity, thereby obtaining 0.671 g of title product as a yellow solid with melting point 113-114° C. (74% yield).

Workup

  1. extractionextracted with ethyl acetate (3×75 ml)
  2. customThe organic phase was dried
  3. customthe solvents were evaporated off under reduced pressure
  4. customThe resulting crude was purified by chromatography through a silica gel column
  5. washeluting with n-hexane
  6. temperatureethyl acetate mixtures of increasing polarity

Sources & evidence

ORD record
ord-adbacfefd2514e7a80d62e362bb51d99
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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