HCID 18712270, compound → HCID 62402682, compound

HRID 1050720Notes

Reaction equation

HRID 1050720 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([NH:9][C:10]([C:12]1[S:16][C:15]([CH3:17])=[N:14][C:13]=1[CH3:18])=O)[CH3:8]>O1CCCC1>[CH3:17][C:15]1[S:16][C:12]([CH2:10][NH:9][CH2:7][CH3:8])=[C:13]([CH3:18])[N:14]=1

Participants

4

Reactant 2

HCID 18712270HCID 18712270, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 62402682HCID 62402682, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.8 g of lithium aluminum hydride and 20 mL of tetrahydrofuran were added in a 150 mL of single-neck flask equipped with a magnetic stirrer. After stirred for 0.5 to 1.0 hour under ice bath cooling, 1.5 g of N-ethyl-2,4-dimethylthiazole-5-carboxamide in 10 mL of tetrahydrofuran solution are added dropwise, and reacted at the same temperature for 0.5 to 10 hours, and then for 1 to 2 hours at room temperature. The reaction mixture was then extracted with ethyl acetate, the organic layer was separated while the aqueous layer was extracted with ethyl acetate twice. The organic phases were combined, and dried over anhydrous sodium sulfate after washed with an iced aqueous sodium chloride solution twice, then remove the solvent under reduced pressure to obtain 1.0 g of 2,4-dimethyl-5-ethylaminomethylthiazole which was used in the next step directly without purification.

Workup

  1. customequipped with a magnetic stirrer
  2. temperaturecooling
  3. customreacted at the same temperature for 0.5 to 10 hours
  4. waitfor 1 to 2 hours at room temperature
  5. extractionThe reaction mixture was then extracted with ethyl acetate
  6. customthe organic layer was separated while the aqueous layer
  7. extractionwas extracted with ethyl acetate twice
  8. dry with materialdried over anhydrous sodium sulfate
  9. washafter washed with an iced aqueous sodium chloride solution twice
  10. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-dab41ea18a4f4b09b7a67c6010d45e7c
Source dataset
uspto-grants-2016_07
Patent number
US09386769B2

Reaction notes

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