Dimethylamine → Ethyl 2-cyano-3-(dimethylamino)prop-2-enoate

HRID 2255793Notes

Reaction equation

HRID 2255793 reaction equation
[CH3:1][NH:2][CH3:3].[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])#[N:5].[OH-].[Na+].[C:14]1(C)C=CC=CC=1>>[CH3:1][N:2]([CH:14]=[C:6]([C:4]#[N:5])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:3]

Participants

5

Reactant 4

HCID 674DimethylamineHCID 1140TolueneHCID 7764Ethyl cyanoacetateHCID 14798Sodium Hydroxide

Product 1

HCID 274128Ethyl 2-cyano-3-(dimethylamino)prop-2-enoateYield 93%

Conditions

Temperature
20 °C

Procedure

5.5 g of dimethylamine were condensed with 20.9 g of methoxymethyleneiminium methylsulphate at 0° C. After stirring for 1 hour at 20° C., excess dimethylamine and 70% of the resulting methanol were removed in vacuo. Analogously to Example 1, the salt obtained was reacted with 11.4 g of ethyl cyanoacetate and 4.0 g of NaOH in 140 ml of toluene. 93% of ethyl dimethylaminomethylenecyano-acetate were obtained, together with 1.2% of the corresponding methyl ester.

Workup

  1. customexcess dimethylamine and 70% of the resulting methanol were removed in vacuo
  2. customAnalogously to Example 1, the salt obtained

Sources & evidence

ORD record
ord-ac039ce1701846b5b9325fee84f94c89
Source dataset
uspto-grants-1993_08
Patent number
US05241099

Reaction notes

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