Lawesson's reagent → Tert-butyl ((5-methyl-1,3,4-thiadiazol-2-yl)methyl)carbamate

HRID 1894714Notes

Reaction equation

HRID 1894714 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]([NH:11][NH:12][C:13](=O)[CH3:14])=O)([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>C1COCC1>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[S:26][C:13]([CH3:14])=[N:12][N:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 59892150tert-Butyl (2-(2-acetylhydrazinyl)-2-oxoethyl)carbamate

Product 1

HCID 59892191Tert-butyl ((5-methyl-1,3,4-thiadiazol-2-yl)methyl)carbamateYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 37.5 mL THF solution of tert-butyl[2-(2-acetylhydrazino)-2-oxoethyl]carbamate (496 mg, 2.15 mmol) was added Lawesson's reagent (900 mg, 2.23 mmol). The resulting reaction mixture was heated to reflux for 3 hr. The reaction was concentrated and chromatographed on silica gel eluting with a gradient solvent mixture of AcOEt & dichloromethane to give the title compound as white crystalline solid (391 mg).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 3 hr
  4. concentrationThe reaction was concentrated
  5. customchromatographed on silica gel eluting with a gradient solvent mixture of AcOEt & dichloromethane

Sources & evidence

ORD record
ord-0f2d04f8425f410aaa6f0dee9c379248
Source dataset
uspto-grants-2013_08
Patent number
US08513289B2

Reaction notes

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