1,1'-Carbonyldiimidazole → HCID 59026765, compound

HRID 658388Notes

Reaction equation

HRID 658388 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:18]=[N:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:31][NH:32][C:33]([NH2:35])=[S:34]>O>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:18]=[N:17][CH:16]=[CH:15][C:11]=1[C:12]([NH:31][NH:32][C:33](=[S:34])[NH2:35])=[O:14]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 2723789ThiosemicarbazideHCID 590267913-((2-Fluoro-4-iodophenyl)amino)isonicotinic acid

Product 1

HCID 59026765HCID 59026765, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-[(2-fluoro-4-iodophenyl)amino]isonicotinic acid (360 mg; 1.01 mmol) was added 1,1′-carbonylbis(1H-imidazole) (196 mg; 1.21 mmol). The mixture was stirred overnight. The dark yellow colored solution was treated with thiosemicarbazide (110 mg mg; 1.21 mmol). The reaction mixture was stirred at room temperature overnight. Water (10 mL) was added, and extracted with ethyl acetate. Concentrated and purified on Flashmaster to obtain 2-{3-[(2-fluoro-4-iodophenyl)amino]isonicotinoyl}hydrazine carbothioamide. (300 mg, 69%) MS m/z: 432 M+1

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. concentrationConcentrated
  4. custompurified on Flashmaster

Sources & evidence

ORD record
ord-26ecebdfade84b80acfd5f5982bfd355
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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