Lawesson's reagent → HCID 86673534, compound

HRID 874968Notes

Reaction equation

HRID 874968 reaction equation
[C:1]([CH:4]1[N:9]([CH3:10])[CH2:8][CH2:7][N:6]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:5]1)(=O)[NH2:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:27])=CC=1>C1(C)C=CC=CC=1>[C:1]([CH:4]1[N:9]([CH3:10])[CH2:8][CH2:7][N:6]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:5]1)(=[S:27])[NH2:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 231459204-(t-Butoxycarbonyl)-1-methylpiperazine-2-carboxamide

Product 1

HCID 86673534HCID 86673534, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl 3-carbamoyl-4-methylpiperazine-1-carboxylate (400 mg, 1.64 mmol) was dissolved in toluene (20 mL) and Lawesson reagent (332 mg, 0.82 mmol) was added. The reaction mixture was heated to reflux for 5 h. Solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 10-15% MeOH in CHCl3) to afford tert-butyl 3-carbamothioyl-4-methylpiperazine-1-carboxylate (0.17 g, yield 40%) as pale yellow liquid. 1H NMR (300 MHz, CDCl3) δ 8.16 (br s, 1H), 7.47 (br s, 1H), 4.28-4.21 (m, 1H), 4.06-3.99 (m, 1H), 3.62 (m, 1H), 3.18-3.13 (dd, J=10.2 Hz, 4.1 Hz, 1H), 2.89-2.82 (m, 2H), 2.52-2.47 (dd, J=11.5 Hz, 3.4 Hz, 1H), 2.26 (s, 3H), 1.47 (s, 9H). MS (ESI) m/z: Calculated for C11H21N3O2S: 259.14. found: 260.2 (M+H)+

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 h
  3. customSolvent was removed under reduced pressure
  4. customthe crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 10-15% MeOH in CHCl3)

Sources & evidence

ORD record
ord-de2617fda6c04b889e670b8c74acd34a
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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