Potassium thiocyanate → 3-Benzyl-1,2,4-thiadiazol-5-amine

HRID 600988Notes

Reaction equation

HRID 600988 reaction equation
Cl[NH:2][C:3](=[NH:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[S-:12][C:13]#[N:14].[K+]>CO.C(OCC)(=O)C>[CH2:4]([C:3]1[N:11]=[C:13]([NH2:14])[S:12][N:2]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 516872Potassium thiocyanateHCID 178510797HCID 178510797, compound

Product 1

HCID 6055933-Benzyl-1,2,4-thiadiazol-5-amineYield 53%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

N-Chloro-2-phenyl-acetamidine (154 mg, 0.92 mmol) was dissolved in methanol (4.6 mL) and cooled to 0° C. then potassium thiocyanate (89 mg, 0.92 mmol) was added and it was stirred for 1 h. The mixture was diluted with ethyl acetate (50 mL), stirred for 5 min and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography (Merck silica gel 60, 40-63 μm; 50% ethyl acetate/hexanes) to afford 3-benzyl-[1,2,4]thiadiazol-5-ylamine (93 mg, 53%) as an off-white solid: H1-NMR (400 MHz, CDCl3) δ=4.02 (2H, s), 5.94 (2H, br), 7.28 (5H, m).

Workup

  1. stirringstirred for 5 min
  2. filtrationfiltered
  3. customThe filtrate was evaporated in vacuo
  4. customthe residue was purified by flash column chromatography (Merck silica gel 60, 40-63 μm; 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6a28a582b97949039fd475a6138acf89
Source dataset
uspto-grants-2011_03
Patent number
US07902248B2

Reaction notes

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