Ammonia → 2-(Amino(methylthio)methylene)malononitrile

HRID 1438847

Reaction equation

HRID 1438847 reaction equation
[NH3:1].[C:2]([C:4](=[C:7](SC)[S:8][CH3:9])[C:5]#[N:6])#[N:3]>C(O)C>[NH2:1][C:7]([S:8][CH3:9])=[C:4]([C:5]#[N:6])[C:2]#[N:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 992292-(Bis(methylsulfanyl)methylidene)propanedinitrile

Product 1

HCID 44092332-(Amino(methylthio)methylene)malononitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

At 15°, 650 ml of ethanol was saturated with gaseous ammonia. Seventy-three and three-tenths grams of 2-cyano-3,3-bis(methylthio)propenenitrile were added portionwise during 10 minutes. The reaction mixture was heated to 78° during 15 minutes. The slurry was allowed to cool to ambient temperature, then cooled to 10°. The solid was collected by filtration and washed with cold ethanol to give, when dried, m.p. 228°-229° (Literature m.p. 229°-230°, R. Gompper and W. Topel, Ber. 95, 2871 (1902)).

Workup

  1. customAt 15°
  2. temperatureThe reaction mixture was heated to 78° during 15 minutes
  3. temperaturecooled to 10°
  4. filtrationThe solid was collected by filtration
  5. washwashed with cold ethanol
  6. customto give
  7. customwhen dried

Sources & evidence

ORD record
ord-3b3b2c3b2b964d05b86e12fe5dbb59e2
Source dataset
uspto-grants-1977_11
Patent number
US04057416

Linked notes

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