Ammonia → HCID 15020519, compound

HRID 1438853Notes

Reaction equation

HRID 1438853 reaction equation
[NH3:1].[C:2]([C:4](=[C:7](SCC)[S:8][CH2:9][CH3:10])[C:5]#[N:6])#[N:3]>C(O)C>[NH2:1][C:7]([S:8][CH2:9][CH3:10])=[C:4]([C:5]#[N:6])[C:2]#[N:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 161256Propanedinitrile, [bis(ethylthio)methylene]-

Product 1

HCID 15020519HCID 15020519, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into 2.0 liters of ethanol, previously saturated with ammonia, was added 378 g of 2-cyano-3,3-bis(ethylthio)propenenitrile. The mildly exothermic reaction warmed the mixture to 38°. The mixture was stirred at ambient temperature for 0.5 hour, then heated under reflux (ca 55°) for 1.0 hour. The mixture was concentrated by distillation of about one liter of solvent. To the mixture was added 1.5 liters of ice-water and the mixture was cooled in an ice-bath. The yellow solid was isolated and dried to give 223 g of 3-amino-2-cyano-3-(ethylthio)propenenitrile, m.p. 180°-182°. The nmr spectrum was consistent with the assigned structure.

Workup

  1. customThe mildly exothermic reaction
  2. temperaturewarmed the mixture to 38°
  3. temperatureheated
  4. temperatureunder reflux (ca 55°) for 1.0 hour
  5. concentrationThe mixture was concentrated by distillation of about one liter of solvent
  6. additionTo the mixture was added 1.5 liters of ice-water
  7. temperaturethe mixture was cooled in an ice-bath
  8. customThe yellow solid was isolated
  9. customdried

Sources & evidence

ORD record
ord-c41c172606ab4c4f887573ae6fdcce6d
Source dataset
uspto-grants-1977_11
Patent number
US04057416

Reaction notes

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