4-Chlorophenyl isothiocyanate → tert-Butyl 4-{[(4-chlorophenyl)amino]carbonothioyl}-1,4-diazepane-1-carboxylate

HRID 20278

Reaction equation

HRID 20278 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[S:10])=[CH:4][CH:3]=1.[C:11]([N:18]1[CH2:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:21]2[CH2:22][CH2:23][CH2:24][N:18]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:19][CH2:20]2)=[S:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 164804-Chlorophenyl isothiocyanateHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 59347509tert-Butyl 4-{[(4-chlorophenyl)amino]carbonothioyl}-1,4-diazepane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-chlorophenyl isothiocyanate (5.0 g, 29.95 mmol), and BOC-homopiperazine (6.0 g, 29.95 mmol) in ethanol (50 mL) was stirred at room temperature for 2 hours. The mixture was evaporated under reduced pressure, the residue was partitioned between ethyl acetate and water and the layers were separated. The organic phase was dried over MgSO4 and evaporated under reduced pressure to give the title compound as a white foam.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. customthe layers were separated
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-daa6eab60c9e4f4fa2b20aee2c27aaac
Source dataset
uspto-grants-2010_06
Patent number
US07745630B2

Linked notes

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