Ammonium Hydroxide → (1-Amino-2-methylpropylidene)propanedinitrile

HRID 437707Notes

Reaction equation

HRID 437707 reaction equation
Cl[C:2]([CH:8]([CH3:10])[CH3:9])=[C:3]([C:6]#[N:7])[C:4]#[N:5].[OH-].[NH4+:12]>C(O)C>[NH2:12][C:2]([CH:8]([CH3:10])[CH3:9])=[C:3]([C:6]#[N:7])[C:4]#[N:5]

Participants

4

Reactant 2

HCID 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 191.3 g of 3-chloro-2-cyano-4-methyl- 2-pentenenitrile in 300 ml of ethanol was added slowly, maintaining the temperature below 40°, during 1.3 hours, to a mixture of 800 ml of concentrated ammonium hydroxide and 1000 ml of ethanol. The mixture was stirred for 3 hours, then poured over 2000 ml of ice. The solid was collected, washed with water and dried to obtain 122.0 g of 3-amino-2-cyano-4-methyl-2-pentenenitrile, mp 186°-188°.

Workup

  1. temperaturemaintaining the temperature below 40°
  2. customThe solid was collected
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-d699e9f94c074193b7b2777597a0a375
Source dataset
uspto-grants-1977_06
Patent number
US04032322

Reaction notes

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