Water → HCID 54394974, compound

HRID 638618Notes

Reaction equation

HRID 638618 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=[CH:6][C:7]=1[CH2:8][N:9]1[CH:13]=[CH:12][N:11]=[CH:10]1.[NH2:21][CH2:22]CN.O>CN(C)C=O>[C:22]([C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=[CH:6][C:7]=1[CH2:8][N:9]1[CH:13]=[CH:12][N:11]=[CH:10]1)#[N:21]

Participants

5

Reactant 3

HCID 962WaterHCID 3301EthylenediamineHCID 53725360HCID 53725360, compound

Product 1

HCID 54394974HCID 54394974, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 3-[3-bromo-4-(imidazol-1-ylmethyl)phenyl]prop-2-enoate (0.2 g) and cuprous cyanide (0.07 g) in dry N,N-dimethylformamide (1 ml) was stirred and heated under reflux for 8 h. The hot reaction mixture was poured into a stirred solution of 1,2-diaminoethane (0.3 ml) and water (1.5 ml). The reaction mixture was filtered, and the residue was washed with hot benzene 2×8 ml. The organic layer was separated, and the residue was washed with more hot benzene (10 ml). The benzene solutions were combined, dried (MgSO4) and concentrated to afford a brown oil. The oil was purified using `flash` chromatography and chloroform/methanol 9:1 as eluant. The product fractions were combined and concentrated to afford ethyl 3-[3-cyano-4-(imidazol-1-ylmethyl)phenyl]prop-2-enoate as a brown oil. I.R. (CHCl3 film) vC=N: 2230 cm-1

Workup

  1. temperatureheated
  2. temperatureunder reflux for 8 h
  3. filtrationThe reaction mixture was filtered
  4. washthe residue was washed with hot benzene 2×8 ml
  5. customThe organic layer was separated
  6. washthe residue was washed with more hot benzene (10 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto afford a brown oil
  10. customThe oil was purified
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-d9c7b18e3da842949cc495664e38b2b5
Source dataset
uspto-grants-1985_12
Patent number
US04562199

Reaction notes

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