Isoamyl Nitrite → N-benzyl-2-cyano-4-methylthiazole-5-carboxamide

HRID 2381797Notes

Reaction equation

HRID 2381797 reaction equation
N[C:2]1[S:3][C:4]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[C:5]([CH3:7])[N:6]=1.[Cu](C#N)[C:19]#[N:20].N(OCCC(C)C)=O>C(#N)C.C(OCC)(=O)C>[CH2:11]([NH:10][C:8]([C:4]1[S:3][C:2]([C:19]#[N:20])=[N:6][C:5]=1[CH3:7])=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 8053Isoamyl NitriteHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acidHCID 178418260HCID 178418260, compound

Product 1

HCID 68492000N-benzyl-2-cyano-4-methylthiazole-5-carboxamideYield 29%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-N-benzyl-4-methylthiazole-5-carboxamide (0.50 g, 2.02 mmol) in acetonitrile (50 mL) was added copper cyanide (0.36 g, 4.04 mmol) and isoamyl nitrite (0.54 mL, 4.04 mmol). The reaction mixture was heated to reflux for 1 hour, cooled to ambient temperature, diluted with ethyl acetate and washed with water and brine. The organic solution was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography to afford N-benzyl-2-cyano-4-methylthiazole-5-carboxamide in 29% yield (0.15 g): 1H NMR (300 MHz, CDCl3) δ 7.48-7.18 (m, 5H), 6.87 (br s, 1H), 4.49 (d, J=5.8 Hz, 2H), 2.69 (s, 3H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. washwashed with water and brine
  4. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b566d7da23224e2a85f4956decc78a1c
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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