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

HRID 46554

Reaction equation

HRID 46554 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 the 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. customthe evaporated 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-5552638b815740ab94b640be03e43efe
Source dataset
uspto-grants-1979_11
Patent number
US04173650

Linked notes

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