Lawesson's reagent → 2-(tert-Butyl)-5-methyl-1,3,4-thiadiazole

HRID 448027Notes

Reaction equation

HRID 448027 reaction equation
[C:1]([NH:4][NH:5][C:6](=O)[C:7]([CH3:10])([CH3:9])[CH3:8])(=O)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:21])=CC=1>O1CCCC1>[C:7]([C:6]1[S:21][C:1]([CH3:2])=[N:4][N:5]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 23525705N'-acetyl-2,2-dimethylpropanohydrazide

Product 1

HCID 229435972-(tert-Butyl)-5-methyl-1,3,4-thiadiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the product from Example 50A (158 mg, 1 mmol) and Lawesson's reagent (808 mg, 2 mmol) in tetrahydrofuran (4 mL) was heated at reflux for 2 hours. The solution was concentrated, dissolved in dichloromethane (15 mL) and washed with saturated sodium bicarbonate solution (10 mL). The resulting organic layer was passed through a silica pad and washed with dichloromethane and ethyl acetate (10:1). The solvent was evaporated to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.39 (s, 9 H) 2.67 (s, 3 H); MS (ESI) m/z 157 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. concentrationThe solution was concentrated
  4. dissolutiondissolved in dichloromethane (15 mL)
  5. washwashed with saturated sodium bicarbonate solution (10 mL)
  6. washwashed with dichloromethane and ethyl acetate (10:1)
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-f61e161cd16d467b82426c41be70e703
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Reaction notes

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