Water → (1-Amino-2-methylpropylidene)propanedinitrile

HRID 437697Notes

Reaction equation

HRID 437697 reaction equation
Cl[C:2]([CH:8]([CH3:10])[CH3:9])=[C:3]([C:6]#[N:7])[C:4]#[N:5].[OH-].[NH4+:12].O>C(O)C>[NH2:12][C:2]([CH:8]([CH3:10])[CH3:9])=[C:3]([C:6]#[N:7])[C:4]#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 23513711(1-Chloro-2-methylpropylidene)propanedinitrile

Product 1

HCID 21426735(1-Amino-2-methylpropylidene)propanedinitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 530.5 g of 3-chloro-2-cyano-4-methyl-2-pentenenitrile in 515 ml of ethanol was added dropwise during one hour to a stirred solution of 2,400 ml of concentrated ammonium hydroxide in 1,560 ml of ethanol while maintaining the reaction mixture at 35°-40° with an ice-water bath. The reaction mixture was stirred for 3.5-4 hours and was poured into 6.5 liters of ice and water. The mixture was stirred until all the ice had melted (approximately thirty minutes). The precipitate was collected by filtration. The filter cake was washed with two 1500-ml portions of water and air-dried on the filter. After the drying the 400 g of 3-amino-2-cyano-4-methyl-2-pentenenitrile, mp 182°-184°, was used in the next synthesis step without further purification.

Workup

  1. temperaturewhile maintaining the reaction mixture at 35°-40° with an ice-water bath
  2. custom(approximately thirty minutes)
  3. filtrationThe precipitate was collected by filtration
  4. washThe filter cake was washed with two 1500-ml portions of water
  5. customair-dried on the filter
  6. customAfter the drying the 400 g of 3-amino-2-cyano-4-methyl-2-pentenenitrile, mp 182°-184°, was used in the next synthesis step without further purification

Sources & evidence

ORD record
ord-af24a336ad224b81bcd8223dacce0594
Source dataset
uspto-grants-1977_06
Patent number
US04032321

Reaction notes

Loading…