4-Chlorophenyl isothiocyanate → N-(4-chlorophenyl)-3-methylpiperazine-1-carbothioamide

HRID 20275

Reaction equation

HRID 20275 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[S:10])=[CH:4][CH:3]=1.[CH3:11][CH:12]1[CH2:17][NH:16][CH2:15][CH2:14][NH:13]1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:16]2[CH2:15][CH2:14][NH:13][CH:12]([CH3:11])[CH2:17]2)=[S:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 164804-Chlorophenyl isothiocyanateHCID 660572-Methylpiperazine

Product 1

HCID 59347497N-(4-chlorophenyl)-3-methylpiperazine-1-carbothioamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-chlorophenyl isothiocyanate (8.0 g, 47.17 mmol) in dichloromethane (250 mL) was added dropwise over 30 minutes to an ice cooled solution of 2-methylpiperazine (9.45 g, 94.33 mmol) in dichloromethane (250 mL). Once the addition was complete, the reaction was stirred at room temperature for an hour. The reaction was then washed with water (3×), dried over MgSO4 and concentrated under reduced pressure, to give the title compound as a white solid, 11.8 g.

Workup

  1. additionOnce the addition
  2. washThe reaction was then washed with water (3×)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5f9a14faca964707886135ffa8096e54
Source dataset
uspto-grants-2010_06
Patent number
US07745630B2

Linked notes

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