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

HRID 704518Notes

Reaction equation

HRID 704518 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[C:11]([CH2:13][C:14]#[N:15])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19]OC(OC)OC.[CH3:26][NH:27][CH3:28]>C(O)C>[O:1]([C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[C:11]([C:13](=[CH:26][N:27]([CH3:19])[CH3:28])[C:14]#[N:15])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 9005Trimethyl orthoformateHCID 198735383-Phenoxybenzoylacetonitrile

Product 1

HCID 540996322-(3-Phenoxybenzoyl)-3-dimethylaminoacrylonitrileYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

3-Phenoxybenzoylacetonitrile (4 g) and trimethylorthoformate (30 ml) was stirred and heated to 80° C. for 2 hours. After cooling to 0° C., an excess of dimethylamine in ethanol solution was added and the mixture stirred for 2 hours at room temperature. The volatiles were then removed in vacuo and the residue chromatographed on a silica gel column using 5% methanol-dichloromethane (v/v) as eluant to give the title compound (3.2 g, 65%) as a white solid of m.p. 80°-82° C.

Workup

  1. temperatureAfter cooling to 0° C.
  2. customThe volatiles were then removed in vacuo
  3. customthe residue chromatographed on a silica gel column

Sources & evidence

ORD record
ord-bbb9496a3cd34ccabd4155e444978852
Source dataset
uspto-grants-1991_01
Patent number
US04988385

Reaction notes

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