1,3-Dichloro-2-isothiocyanatobenzene → N-(2,6-Dichlorophenyl)-4-(pyrazin-2-yl)piperazine-1-carbothioamide

HRID 544484Notes

Reaction equation

HRID 544484 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.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=1[N:21]=[C:22]=[S:23]>CCOCC>[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=1[NH:21][C:22]([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:23]

Participants

4

Reactant 2

HCID 1232391,3-Dichloro-2-isothiocyanatobenzeneHCID 27346391-Piperazinylpyrazine

Product 1

HCID 20459211N-(2,6-Dichlorophenyl)-4-(pyrazin-2-yl)piperazine-1-carbothioamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 4.92 g. of 1-(2-pyrazinyl)piperazine in 50 ml. of anhydrous ether is added dropwise a solution of 6.12 g. of 2,6-dichlorophenyl isothiocyanate in 50 ml. of anhydrous ether over 10 minutes. The mixture is stirred for 15 minutes and the resulting solid collected. This solid is dissolved with heat in a mixture of 200 ml. of acetone and 150 ml. of methanol and then cooled. The resulting solid is collected giving 5.29 g. of the desired product as white crystals, m.p. 225°-227° C.

Workup

  1. customthe resulting solid collected
  2. dissolutionThis solid is dissolved
  3. temperaturewith heat in a mixture of 200 ml
  4. temperatureof methanol and then cooled
  5. customThe resulting solid is collected
  6. customgiving 5.29 g

Sources & evidence

ORD record
ord-6db896f2eea74c95ac7c2c0125c4e4f9
Source dataset
uspto-grants-1984_05
Patent number
US04450272

Reaction notes

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