Triethylamine → HCID 18712270, compound

HRID 1050719Notes

Reaction equation

HRID 1050719 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8]([O:10]CC)=O)=[C:5]([CH3:7])[N:6]=1.Cl.[CH2:14]([NH2:16])[CH3:15].C(N(CC)CC)C>C(O)C>[CH2:14]([NH:16][C:8]([C:4]1[S:3][C:2]([CH3:1])=[N:6][C:5]=1[CH3:7])=[O:10])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 603810Ethyl 2,4-dimethylthiazole-5-carboxylate

Product 1

HCID 18712270HCID 18712270, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

3.0 g of ethyl 2,4-dimethylthiazole-5-carboxylate, 7.0 g of ethylamine hydrochloride, 6.0 g of triethylamine, and 100 mL of ethanol were added into a 250 mL of high-pressure reactor. And the reaction mixture was heated to 120-160° C. and stirred for 20 to 30 hours, and 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 1.5 g N-ethyl-2,4-dimethylthiazole-5-carboxamide which was used in the next step directly without purification.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic layer was separated while the aqueous layer
  3. extractionwas extracted with ethyl acetate twice
  4. dry with materialdried over anhydrous sodium sulfate
  5. washafter washed with an iced aqueous sodium chloride solution twice
  6. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-ad7988916cd4472db2bcdd322c9dc517
Source dataset
uspto-grants-2016_07
Patent number
US09386769B2

Reaction notes

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