Formic Acid → HCID 178423431, compound

HRID 2381856Notes

Reaction equation

HRID 2381856 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:12][C:13]([C:17]([NH:19][NH2:20])=[NH:18])=[CH:14][C:15]=1[CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:21](O)=O>>[CH2:1]([NH:8][C:9]([C:11]1[S:12][C:13]([C:17]2[N:18]=[CH:21][NH:20][N:19]=2)=[CH:14][C:15]=1[CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 178426647HCID 178426647, compound

Product 1

HCID 178423431HCID 178423431, compoundYield 84%

Procedure

N-benzyl-5-(hydrazinyl(imino)methyl)-3-methylthiophene-2-carboxamide (0.65 g, 2.24 mmol) in formic acid (20 mL) was stirred at reflux for 2 h. The reaction mixture was allowed to cool to ambient temperature, and then was concentrated in vacuo. The residue was dissolved in saturated aqueous sodium bicarbonate solution (50 mL) and extracted with 5% methanol in dichloromethane (3×75 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with dichloromethane in hexanes to afford the title compound as a light yellow solid (0.56 g, 84%): 1H NMR (300 MHz, CDCl3) δ 8.23 (s, 1H), 7.48 (s, 1H), 7.39-7.30 (m, 5H), 6.14 (br s, 1H), 4.63 (d, J=5.4 Hz, 2H), 2.54 (s, 3H); MS (ES+) m/z 299.2 (M+1).

Workup

  1. temperatureat reflux for 2 h
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe residue was dissolved in saturated aqueous sodium bicarbonate solution (50 mL)
  4. extractionextracted with 5% methanol in dichloromethane (3×75 mL)
  5. dry with materialThe combined organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with dichloromethane in hexanes

Sources & evidence

ORD record
ord-3d281446e3f04377a0527bc799891bdf
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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