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

HRID 616490Notes

Reaction equation

HRID 616490 reaction equation
N.[C:2]([C:4](=[C:7](SC)[S:8][CH3:9])[C:5]#[N:6])#[N:3].CS.C(#[N:17])C=C>C(O)C>[NH2:17][C:7]([S:8][CH3:9])=[C:4]([C:5]#[N:6])[C:2]#[N:3]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 878MethanethiolHCID 7855AcrylonitrileHCID 992292-(Bis(methylsulfanyl)methylidene)propanedinitrile

Product 1

HCID 44092332-(Amino(methylthio)methylene)malononitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Two liters of ethanol were saturated with ammonia gas at 15°. At ambient temperature, 278.3 g of 2-cyano-3,3-bis(methylthio)propenenitrile were added portionwise. A sodium hydroxide trap was used to trap the methyl mercaptan by-product. After complete addition of the propenenitrile the reaction mixture was cooled to approximately 10°. The solid which separated was collected by filtration and washed with cold ethanol to give, after drying, 206.3 g of white 3-amino-2-cyano-3-(methylthio)propenenitrile, m.p. 228°-230°. The nmr was consistent with the assigned structure.

Workup

  1. customA sodium hydroxide trap was used to trap
  2. temperaturewas cooled to approximately 10°
  3. customThe solid which separated
  4. filtrationwas collected by filtration
  5. washwashed with cold ethanol
  6. customto give
  7. customafter drying

Sources & evidence

ORD record
ord-ff596e9f27bf4f31a60fdb7b1c4ade32
Source dataset
uspto-grants-1978_02
Patent number
US04075001

Reaction notes

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