Triethylamine → 2-(3-Phenoxybenzoyl)-3-dimethylaminoacrylonitrile

HRID 704519Notes

Reaction equation

HRID 704519 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11](Cl)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][N:18]([CH3:23])[CH:19]=[CH:20][C:21]#[N:22].C(N(CC)CC)C>O1CCOCC1>[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([C:20](=[CH:19][N:18]([CH3:23])[CH3:17])[C:21]#[N:22])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 974973-(Dimethylamino)prop-2-enenitrileHCID 27603413-Phenoxybenzoyl chloride

Product 1

HCID 540996322-(3-Phenoxybenzoyl)-3-dimethylaminoacrylonitrileYield 36.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-phenoxybenzoyl chloride (6.9 g), 3-dimethylaminoacrylonitrile (2 g) and triethylamine (4 g) in dry dioxan (50 ml) was refluxed for 6 hours under a nitrogen atmosphere. After standing at room temperature overnight, the dioxan was evaporated in vacuo and dichloromethane added to the residue. The extracts were washed with water, 2N NaOH, brine and finally dried over MgSO4. After filtration and evaporation of the dichloromethane, the residue was purified on a silica gel column using 5% methanol-dichloromethane as eluant to give the title compound (2.2 g, 36%) as a white solid of m.p. 80°-82 C. (identical to that described in Example 46).

Workup

  1. temperaturewas refluxed for 6 hours under a nitrogen atmosphere
  2. customthe dioxan was evaporated in vacuo and dichloromethane
  3. additionadded to the residue
  4. washThe extracts were washed with water, 2N NaOH, brine
  5. dry with materialfinally dried over MgSO4
  6. filtrationAfter filtration and evaporation of the dichloromethane
  7. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-e2e0b2482c2548e487908a9fbb1a3c3d
Source dataset
uspto-grants-1991_01
Patent number
US04988385

Reaction notes

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