Potassium Hydroxide → 5-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-3H-[1,3,4]oxadiazole-2-thione

HRID 658364Notes

Reaction equation

HRID 658364 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:19]=[N:18][CH:17]=[CH:16][C:11]=1[C:12]([NH:14][NH2:15])=[O:13].[CH2:20](S)[SH:21].[OH-].[K+]>CO>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:19]=[N:18][CH:17]=[CH:16][C:11]=1[C:12]1[O:13][C:20](=[S:21])[NH:15][N:14]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 138818MethanedithiolHCID 115888023-[(2-Fluoro-4-iodophenyl)amino]isonicotinohydrazide

Product 1

HCID 248900835-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-3H-[1,3,4]oxadiazole-2-thione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-(2-Fluoro-4-iodo-phenylamino)-isonicotinic acid hydrazide (744 mg, 2.ommol) in methanol (15 mL) were added dithiomethane (0.22 mL, 4.66 mmol), followed by potassium hydroxide (2.51 mL, 2.13 mmol). The reaction mixture was stirred at 60° C. for 7 h. The solvent was evaporated and the residue was dissolved in ethyl acetate (50 mL), washed with Brine (15 mL×3), dried over anhydrous MgSO4, filtered, removed off solvent. Residue was subjected to silica gel column (EtOAc:Hexane=1:1) collected product 210 mg. LC-MS (Method A) [5.71 min; 415(M+1)]

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
  3. washwashed with Brine (15 mL×3)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customremoved off solvent
  7. customcollected product 210 mg
  8. customLC-MS (Method A) [5.71 min; 415(M+1)]

Sources & evidence

ORD record
ord-4000054f32c04ddb82abe45405916ba9
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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