HCID 68494041, compound → N-benzyl-2-cyano-4-methylthiazole-5-carboxamide

HRID 2381778Notes

Reaction equation

HRID 2381778 reaction equation
[Cu][C:2]#[N:3].[CH2:4]([NH:11][C:12]([C:14]1[S:18][C:17](I)=[N:16][C:15]=1[CH3:20])=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CN(C)C=O.O>[CH2:4]([NH:11][C:12]([C:14]1[S:18][C:17]([C:2]#[N:3])=[N:16][C:15]=1[CH3:20])=[O:13])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 68494041HCID 68494041, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 68492000N-benzyl-2-cyano-4-methylthiazole-5-carboxamideYield 41.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of copper(I) cyanide (0.19 g, 2.10 mmol) in anhydrous N,N-dimethylformamide (6 mL) at 150° C. was added N-benzyl-2-iodo-4-methylthiazole-5-carboxamide (0.30 g, 0.84 mmol). The resulting reaction mixture was stirred at same temperature for 10 minutes, and then allowed to cool to ambient temperature and diluted with water (50 mL). The resulting precipitate was filtered, washed with water (50 mL) and ethyl acetate (100 mL). The organic filtrate was washed with water (2×50 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (0-20% ethyl acetate in hexanes) to afford the title compound as a clear oil (0.09 g, 39%): 1H NMR (300 MHz, CDCl3) δ 7.42-7.30 (m, 5H), 6.17 (br s, 1H), 4.63 (d, J=5.6 Hz, 2H), 2.73 (s, 3H); MS (ES−) m/z 256.2 (M−1).

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water (50 mL) and ethyl acetate (100 mL)
  4. washThe organic filtrate was washed with water (2×50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (0-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d1533f3b925c4084a42a80b900d8332b
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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