1,1-Dimethoxyethyl(dimethyl)amine → 2-(p-Fluorobenzoyl)-3-dimethylaminocrotononitrile

HRID 128163

Reaction equation

HRID 128163 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([CH2:8][C:9]#[N:10])=[O:7])=[CH:4][CH:3]=1.CO[C:15](OC)([N:17]([CH3:19])[CH3:18])[CH3:16]>C(Cl)(Cl)Cl>[CH3:19][N:17]([CH3:18])/[C:15](/[CH3:16])=[C:8](/[C:6](=[O:7])[C:5]1[CH:11]=[CH:12][C:2]([F:1])=[CH:3][CH:4]=1)\[C:9]#[N:10]

Participants

4

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 2783172p-Fluorobenzoylacetonitrile

Product 1

HCID 234684972-(p-Fluorobenzoyl)-3-dimethylaminocrotononitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 1.6 g. of p-fluorobenzoylacetonitrile [Pihl et al., Reakts. Sposobnost Org. Soedin. Tartu. Gos. Univ., 5 (1), 27, (1968)] in 30 ml. of chloroform, cooled to -10° C., is added 1.4 g. of N,N-dimethylacetamide dimethylacetal. The reaction mixture is stirred at -10° C. for 2 hours and then evaporated in vacuo to an oil. This oil is dissolved in 150 ml. of benzene and filtered through Magnesol®. The filtrate is evaporated to 50 ml. and petroleum ether is added to effect crystallization. The product is collected by filtration and then recrystallized from benzene-petroleum ether with charcoal treatment giving the desired product.

Workup

  1. additionis added 1.4 g
  2. customevaporated in vacuo to an oil
  3. dissolutionThis oil is dissolved in 150 ml
  4. filtrationof benzene and filtered through Magnesol®
  5. customThe filtrate is evaporated to 50 ml
  6. additionand petroleum ether is added to effect crystallization
  7. filtrationThe product is collected by filtration
  8. customrecrystallized from benzene-petroleum ether with charcoal treatment

Sources & evidence

ORD record
ord-7c5808a82e174b9fa1fa2e1ca3f810ae
Source dataset
uspto-grants-1981_03
Patent number
US04259256

Linked notes

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