Triethylamine → HCID 14084217, compound

HRID 1650340Notes

Reaction equation

HRID 1650340 reaction equation
CN(C)[N:3]=[CH:4][C:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]=1.Cl[C:13](=[CH2:16])[C:14]#[N:15].C(N(CC)CC)C>O1CCOCC1>[C:14]([C:13]1[N:3]=[CH:4][C:5]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:16]=1)#[N:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 701982-ChloroacrylonitrileHCID 56624907HCID 56624907, compound

Product 1

HCID 14084217HCID 14084217, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

7.6 g cyclohex-1-ene-carboxaldehyde-N,N-dimethylhydrazone, 4.4 g of 2-chloroacrylonitrile and 10.1 g of triethylamine are heated in 75 ml of dioxane for 18 hours to 90° C. The reaction mixture is concentrated by evaporation and the residue is acidified with 1N HCl and extracted three times with chloroform. The combined extracts are dried and concentrated by evaporation and the residue is chromatographed over silica gel. Pale yellow crystals of the title compound are isolated. Melting point: 56°-59° C.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. extractionextracted three times with chloroform
  3. customThe combined extracts are dried
  4. concentrationconcentrated by evaporation
  5. customthe residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-28c11552c60f443eaf6a830b19259fb8
Source dataset
uspto-grants-1990_05
Patent number
US04923993

Reaction notes

Loading…