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

HRID 419849Notes

Reaction equation

HRID 419849 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-37b6b62585d0483cab31f913c1d06d92
Source dataset
uspto-grants-2012_01
Patent number
US08093400B2

Reaction notes

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