Acetone → HCID 178478159, compound

HRID 376249Notes

Reaction equation

HRID 376249 reaction equation
ClC[N:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][CH2:4]1.[NH2:10][C:11]1[S:12][CH:13]=[N:14][N:15]=1.[I-].[Na+].[CH3:18]C(C)=O>>[Cl:9][C:8]1[N:3]=[CH:4][C:5]([CH2:18][N:10]=[C:11]2[NH:15][N:14]=[CH:13][S:12]2)=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 5238Sodium IodideHCID 199091,3,4-Thiadiazol-2-amineHCID 19361563HCID 19361563, compound

Product 1

HCID 178478159HCID 178478159, compoundYield 28%

Procedure

N-Chloromethyl-6-chloropyridine (717 mg (4.43 mM)) (prepared according to the method of J. Het. Chem., 1979, 16, 333-336), 537 mg (5.31 mM) of 2-amino-1,3,4-thiadiazole and 1.99 g (13.29 mM) of sodium iodide were mixed together in 60 mL of acetone and refluxed for 18 hours. The reaction mixture was cooled to room temperature and the solvent was evaporated. The residue was dissolved in a 1:1 mixture of 50 mL of 10% NaOH and 50 mL of methylene chloride. The organic layer was dried (Na2SO4) and the solvent was evaporated. The residue was chromatographed on silica using 2% methanol in methylene chloride as the eluant. Appropriate fractions were combined to yield 282 mg (28%) of the title product as an oil. 1H-NMR (CDCl3) δ 8.45, (d, 1H, J=2.8 Hz), 7.70 (dd, 1H, J=2.8, 10.7 Hz), 7.60 (s, 1H, J=10.7 Hz), 7.28 (d, 1H, J=10.7 Hz), 5.10 (s, 2H).

Workup

  1. temperaturerefluxed for 18 hours
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in a 1:1 mixture of 50 mL of 10% NaOH and 50 mL of methylene chloride
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customthe solvent was evaporated
  6. customThe residue was chromatographed on silica using 2% methanol in methylene chloride as the eluant

Sources & evidence

ORD record
ord-acbf8165ed484cdeb527728504d76f9d
Source dataset
uspto-grants-2000_02
Patent number
US06020335

Reaction notes

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