Methyl iodide → HCID 12263408, compound

HRID 32362Notes

Reaction equation

HRID 32362 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:10][CH3:11])[S:5][C:6]=1[C:7](=[O:9])[CH3:8].[H-].[Na+].[CH3:14]I>C1COCC1.CCOC(C)=O>[CH3:11][N:10]([CH3:14])[C:4]1[S:5][C:6]([C:7](=[O:9])[CH3:8])=[C:2]([CH3:1])[N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 227441161-(4-Methyl-2-(methylamino)thiazol-5-YL)ethanone

Product 1

HCID 12263408HCID 12263408, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(4-methyl-2-methylamino-thiazol-5-yl)-ethanone (0.40 g, 2.4 mmol) in THF (2 mL) was treated with NaH (0.113 g, 4.7 mmol). After heating at 40° C. for 0.5 h MeI (0.35 g, 2.4 mmol) was added. Heating was continued for a further 2 h. After cooling, the solution was diluted with EtOAc, washed with brine, and dried over MgSO4. The solvent was evaporated to afford 1-(2-dimethylamino-4-methyl-thiazol-5-yl)-ethanone as a yellow solid. 1H-NMR (CDCl3) δ: 2.36 (s, 3H, CH3), 2.51 (s, 3H, CH3), 3.10 (s, 6H, CH3).

Workup

  1. additionwas added
  2. temperatureHeating
  3. temperatureAfter cooling
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-75556bd194b34770aedfa394501cf480
Source dataset
uspto-grants-2008_09
Patent number
US07427627B2

Reaction notes

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