2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → ethyl 3-(N'-benzylidene-N-methylhydrazino)2-cyanoacrylate

HRID 603334Notes

Reaction equation

HRID 603334 reaction equation
[CH:1](=[N:8][NH:9][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[CH:14]=[C:15]([C:21]#[N:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])C>C1(C)C=CC=CC=1>[CH:1](=[N:8][N:9]([CH:14]=[C:15]([C:21]#[N:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 302615Benzaldehyde Methylhydrazone

Product 1

HCID 3751881ethyl 3-(N'-benzylidene-N-methylhydrazino)2-cyanoacrylateYield 90.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

258 g (1.92 mol) of N-benzylidene-/V′-methylhydrazine and 325 g (1.92 mol) of ethyl ethoxy-methylenecyanoacetate were initially charged in 1000 ml of toluene and heated at the boil for 1 hour. After cooling, the mixture was filtered off with suction, which gave 447 g (89.5% of theory) of ethyl 3-(N′-benzylidene-N-methylhydrazino)-2-cyanoacrylate [log P (pH 2.3)=2.31]. The filtrate was allowed to stand for 16 hours and then again filtered off with suction, which gave another 7.7 g (1.5% of theory) of the desired product.

Workup

  1. temperatureheated at the boil for 1 hour
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered off with suction, which

Sources & evidence

ORD record
ord-91005b844035475b889735f129931456
Source dataset
uspto-grants-2011_03
Patent number
US07906656B2

Reaction notes

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