Toluene → 1-(N,N-dimethylamino)-2,3-dicyanoprop-1-ene
Reaction equation
[K].O[CH:3]=[C:4]([C:8]#[N:9])[CH2:5][C:6]#[N:7].C1(C)C=CC=CC=1.Cl.[CH3:18][NH:19][CH3:20]>CN(C=O)C>[CH3:18][N:19]([CH:3]=[C:4]([C:8]#[N:9])[CH2:5][C:6]#[N:7])[CH3:20]Participants
Procedure
A 12 liter three-necked round-bottomed flask, fitted with a mechanical stirrer, water condenser, nitrogen inlet and bubbler, was charged with 877 g (6 moles) of the potassium salt of 1-hydroxy-2,3-dicyanoprop-1-ene in 61 of anhydrous toluene and 300 ml of anhydrous DMF. To this heterogeneous mixture was added 514 g (6.3 moles) of dimethylamine hydrochloride. The mixture was heated to 80° then cooled to room temperature, filtered and the filter cake rinsed with toluene. The filtrate was concentrated under vacuum to yield 933 g containing on 75% weight, 86% yield of an off which partially crystallized at -5° C. An aliquot of the crystalline portion was collected and recrystallized twice from ether to give white crystals, m.p. 49° C. of 1-(N,N-dimethylamino)-2,3-dicyanoprop-1-ene (CIS 1).
Workup
- customA 12 liter three-necked round-bottomed flask, fitted with a mechanical stirrer, water condenser, nitrogen inlet
- temperatureThe mixture was heated to 80°
- filtrationfiltered
- washthe filter cake rinsed with toluene
- concentrationThe filtrate was concentrated under vacuum
- customto yield 933 g
- additioncontaining on 75% weight, 86% yield of an off which
- custompartially crystallized at -5° C
- customAn aliquot of the crystalline portion was collected
- customrecrystallized twice from ether
Sources & evidence
- ORD record
- ord-d16122fa10994e959be8d12cb080d1b3
- Source dataset
- uspto-grants-1996_04
- Patent number
- US05506260
Reaction notes
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