Lawesson's reagent → tert-Butyl (1-carbamothioylcyclopropyl)carbamate

HRID 1040423Notes

Reaction equation

HRID 1040423 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1([C:11](=O)[NH2:12])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1>C1COCC1>[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1([C:11](=[S:24])[NH2:12])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 20825554tert-butyl N-(1-carbamoylcyclopropyl)carbamate

Product 1

HCID 58431174tert-Butyl (1-carbamothioylcyclopropyl)carbamateYield 159.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (1-carbamoyl-cyclopropyl)-carbamic acid tert-butyl ester (1.00 g, 4.99 mmol) in 6 mL of THF was added Lawesson's reagent (1.01 g, 2.50 mmol). The pale yellow cloudy reaction mixture was stirred at room temperature for 6 h and then partitioned between 40 mL of ethyl acetate and 15 mL of 0.5 M NaOH solution. The organic phase was washed with 15 mL each of water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude was purified by flash chromatography on silica gel, eluting with 20-60% EtOAc/hexanes, to give 864 mg (80%) of (1-thiocarbamoyl-cyclopropyl)-carbamic acid tert-butyl ester as a white solid.

Workup

  1. customThe pale yellow cloudy reaction mixture
  2. custompartitioned between 40 mL of ethyl acetate and 15 mL of 0.5 M NaOH solution
  3. washThe organic phase was washed with 15 mL each of water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified by flash chromatography on silica gel
  8. washeluting with 20-60% EtOAc/hexanes

Sources & evidence

ORD record
ord-c21c9dcba03044b98822d0cf6caf7996
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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