Potassium Carbonate → N-benzyl-4-methyl-2-(oxazol-5-yl)thiazole-5-carboxamide

HRID 2381870Notes

Reaction equation

HRID 2381870 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([CH:16]=[O:17])=[N:13][C:12]=1[CH3:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S([CH2:29][N+:30]#[C-:31])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[O:17][CH:31]=[N:30][CH:29]=2)=[N:13][C:12]=1[CH3:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 73213265HCID 73213265, compound

Product 1

HCID 24960064N-benzyl-4-methyl-2-(oxazol-5-yl)thiazole-5-carboxamideYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-benzyl-2-formyl-4-methylthiazole-5-carboxamide (1.09 g, 4.17 mmol) in methanol (60 mL) was added tosylmethyl isocyanide (1.15 g, 5.88 mmol) and potassium carbonate (1.47 g, 10.69 mmol). The reaction mixture was stirred for 50 hours and concentrated in vacuo. The residue was diluted with chloroform 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 the title compound in 63% yield (1.00 g): 1H NMR (300 MHz, CDCl3) δ 7.95 (s, 1H), 7.70 (s, 1H), 7.42-7.26 (m, 5H), 6.06 (t, J=5.6 Hz, 1H), 4.61 (d, J=5.6 Hz, 2H), 2.72 (s, 3H); MS (ES+) m/z 300.1 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with chloroform
  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-d358dede0c0a43e6b24806dbdd18c88f
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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