Ammonia → 3-aMino-2-cyanobut-2-enethioaMide

HRID 635118Notes

Reaction equation

HRID 635118 reaction equation
[C:1](/[C:3](=[C:7](/OCC)\[CH3:8])/[C:4]([NH2:6])=[S:5])#[N:2].C(O)C.[NH3:15].C(OCC)(=O)C>C1(C)C=CC=CC=1>[NH2:15]/[C:7](/[CH3:8])=[C:3](/[C:1]#[N:2])\[C:4]([NH2:6])=[S:5]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 8857Ethyl AcetateHCID 586735589943-20-4

Product 1

HCID 122550733-aMino-2-cyanobut-2-enethioaMide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 3 liter multi-neck flask was equipped with air stirrer, gas inlet, thermometer and condenser. To the flask was charged 2-cyano-3-ethoxythiocrotonamide (68 g, 0.4 mole) and 74 OP ethanol (2 liters). The mixture was then stirred at room temperature. Very little of the solid appeared to dissolve. Ammonia was then bubbled through the reaction mixture. After approximately 15 minutes it became apparent that the starting material was reacting, evidenced by the increased solubility, and after 30 minutes a homogeneous solution resulted. Passage of ammonia through the solution was continued until no more gas was taken up. TLC showed the reaction to be complete, as evidenced by the disappearance of the starting material (silica, eluent 30% ethyl acetate in toluene, Rf product: 0.5, Rf starting material: 0.1).

Workup

  1. customA 3 liter multi-neck flask was equipped with air stirrer, gas inlet
  2. dissolutionto dissolve
  3. customAmmonia was then bubbled through the reaction mixture
  4. customafter 30 minutes a homogeneous solution resulted
  5. customthe reaction

Sources & evidence

ORD record
ord-a52a31bcc9e0457dba508cbc2c992219
Source dataset
uspto-grants-2001_02
Patent number
US06187084B1

Reaction notes

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