2-(Dimethylamino)ethanol → 2-(N,N-dimethylamino)ethyl 2-vinyl-1-cyanocyclopropane-1-carboxylate

HRID 1649583Notes

Reaction equation

HRID 1649583 reaction equation
[CH:1]([CH:3]1[CH2:5][C:4]1([C:11]#[N:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH2:2].[CH3:13][N:14](CCO)[CH3:15].[Na]>>[CH:1]([CH:3]1[CH2:5][C:4]1([C:11]#[N:12])[C:6]([O:8][CH2:9][CH2:10][N:14]([CH3:15])[CH3:13])=[O:7])=[CH2:2]

Participants

4

Reactant 3

HCID 79022-(Dimethylamino)ethanol2×HCID 564450Cyclopropanecarboxylic acid, 1-cyano-2-ethenyl-, ethyl ester2×HCID 5360545Sodium

Product 1

HCID 132453252-(N,N-dimethylamino)ethyl 2-vinyl-1-cyanocyclopropane-1-carboxylate

Procedure

2-(N,N-dimethylamino)ethyl 2-vinyl-1-cyanocyclopropane-1-carboxylate was prepared by reacting essentially equimolar amounts of ethyl 2-vinyl-1-cyanocyclopropane-1-carboxylate and N,N-dimethylaminoethanol. For the reaction, a small amount of sodium metal (1.13 wt. %) was reacted with the N,N-dimethylaminoethanol prior to the addition of the ethyl 2-vinyl-1-cyanocyclopropane-1-carboxylate. The reaction mixture was stirred for 35 minutes after which time gas chromatographic analysis indicated the reaction to be 70% complete. After workup of the reaction mixture, the crude product was vacuum distilled to obtain the 2-(N,N-dimethylamino)ethyl 2-vinyl-1-cyanocyclopropane-1-carboxylate (B.p. 97° C. at 0.015 mm Hg). The infrared spectrum was consistent with the structure. nmr (CDCl3)τ 3.97-4.85(3 vinyl H, mult.); 5.75(2H, tr.); 7.15-7.60(1H(2 ring position, hidden), mult); 7.37(2H, tr.); 7.74(6H,s); 7.85-8.55(2H(3 ring position), mult.).

Workup

  1. custom2-(N,N-dimethylamino)ethyl 2-vinyl-1-cyanocyclopropane-1-carboxylate was prepared
  2. customFor the reaction
  3. customthe reaction
  4. distillationdistilled

Sources & evidence

ORD record
ord-29ae21391902465fb73008cabc54e475
Source dataset
uspto-grants-1983_11
Patent number
US04418202

Reaction notes

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