Methyl isothiocyanate → N-Methyl-4-(pyrazin-2-yl)piperazine-1-carbothioamide

HRID 544481Notes

Reaction equation

HRID 544481 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[CH3:13][N:14]=[C:15]=[S:16]>CCOCC>[CH3:13][NH:14][C:15]([N:10]1[CH2:9][CH2:8][N:7]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)[CH2:12][CH2:11]1)=[S:16]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 27346391-Piperazinylpyrazine

Product 1

HCID 13318687N-Methyl-4-(pyrazin-2-yl)piperazine-1-carbothioamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 6.56 g. of 1-(2-pyrazinyl)piperazine (U.S. Pat. No. 2,606,906) in 40 ml. of anhydrous ether is added a solution of 2.92 g. of methyl isothiocyanate in 40 ml. of anhydrous ether, dropwise over a periodof 10 minutes. This suspension is stirred for one hour and the solid is collected and washed. This solid is dissolved in a mixture of 200 ml. of benzene and 50 ml. of ethanol with heat and then cooled to room temperature over 48 hours. The resulting solid is dissolved in 400 ml. of ethanol:ethyl acetate (1:3), concentrated to 200 ml. and chilled. The resulting solid is collected giving 4.34 g. of the desired product as white crystals, m.p. 197°-200° C.

Workup

  1. customthe solid is collected
  2. washwashed
  3. dissolutionThis solid is dissolved in a mixture of 200 ml
  4. temperatureof ethanol with heat
  5. dissolutionThe resulting solid is dissolved in 400 ml
  6. concentrationof ethanol:ethyl acetate (1:3), concentrated to 200 ml
  7. temperatureand chilled
  8. customThe resulting solid is collected
  9. customgiving 4.34 g

Sources & evidence

ORD record
ord-5173e69078a04f02959ac20aee38727a
Source dataset
uspto-grants-1984_05
Patent number
US04450272

Reaction notes

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