Water → 2-(3-Iodophenyl)-5-methyl-1,3,4-thiadiazole

HRID 1672791Notes

Reaction equation

HRID 1672791 reaction equation
C1(C)C=CC=CC=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:17])=CC=1.[C:30]([NH:33][NH:34][C:35](=O)[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([I:42])[CH:37]=1)(=O)[CH3:31].O>C(OCC)(=O)C>[I:42][C:38]1[CH:37]=[C:36]([C:35]2[S:17][C:30]([CH3:31])=[N:33][N:34]=2)[CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 87949Lawesson's reagentHCID 824395HCID 824395, compound

Product 1

HCID 193499822-(3-Iodophenyl)-5-methyl-1,3,4-thiadiazoleYield 60.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Toluene (4.1 mL) and Lawesson's reagent (366 mg, 0.904 mmol) were added to N′-acetyl-3-iodobenzohydrazide (250 mg, 0.822 mmol) obtained in Step 1, and the mixture was stirred at 120° C. for 1 hour. After cooling, water and ethyl acetate were added to the mixture to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give 2-(3-iodophenyl)-5-methyl-1,3,4-thiadiazole (150 mg, 60%).

Workup

  1. temperatureAfter cooling
  2. customto separate the organic layer
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-57390878c68a49b288a5e393d50076c3
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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