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1,1'-Thiocarbonyldiimidazole → tert-Butyl 4-carbamothioylpiperazine-1-carboxylate

HRID 238661
Notes
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Reaction equation

HRID 238661 reaction equation
[C:1](N1C=CN=C1)([N:3]1C=CN=C1)=[S:2].[N:13]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>O1CCCC1>[NH2:3][C:1](=[S:2])[N:16]1[CH2:17][CH2:18][N:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:15]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 12093220tert-Butyl 4-carbamothioylpiperazine-1-carboxylateYield 56.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of thiocarbonyldiimidazole (2.1 g, 11.8 mmol) in tetrahydrofuran (30 mL) at room temperature, was added 1,1-dimethylethyl 1-piperazinecarboxylate (2 g, 10.75 mmol). The reaction mixture was stirred at room temperature for 2 h and then heated to 55° C. for additional 2 h. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure until approximately 20 mL of tetrahydrofuran remained. The residue was then treated with a 2 M solution of ammonia in methanol (10 mL) and stirred at room temperature for 24 h. The reaction mixture was concentrated under reduced pressure, and the residue was triturated with diethyl ether (25 mL) to give a white precipitate. The precipitate was filtered and dried to give 1.5 g of the title compound as a white solid.

Workup

  1. temperatureheated to 55° C. for additional 2 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure until approximately 20 mL of tetrahydrofuran
  4. additionThe residue was then treated with a 2 M solution of ammonia in methanol (10 mL)
  5. stirringstirred at room temperature for 24 h
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. customthe residue was triturated with diethyl ether (25 mL)
  8. customto give a white precipitate
  9. filtrationThe precipitate was filtered
  10. customdried

Sources & evidence

ORD record
ord-cda6c91cb0ba4bd4bdd248c7d4410322
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08642634B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes