Tetrahydrofuran → HCID 22272833, compound

HRID 1064799Notes

Reaction equation

HRID 1064799 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[C:10]([S:18][CH3:19])=[N:11][C:12]([CH3:17])=[CH:13][C:14]=1[S:15][CH3:16].[CH2:20]1C[O:23][CH2:22][CH2:21]1>O>[CH3:19][S:18][C:10]1[C:9]([NH:8][C:22](=[O:23])[CH:21]=[CH2:20])=[C:14]([S:15][CH3:16])[CH:13]=[C:12]([CH3:17])[N:11]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 99903926-Methyl-2,4-bis-methylsulfanylpyridin-3-ylamine

Product 1

HCID 22272833HCID 22272833, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (277 mg, 2.75 mmol) was added to a solution of 3-amino-2,4-bis(methylthio)-6-methylpyridine (500 mg, 2.50 mmol) in THF (10 ml), then a solution of acryloyl acid chloride (225 mg, 2.50 mmol) in THF (3 ml) was gradually dropped thereinto and the mixture was stirred for 14 hours. The reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with a sodium chloride solution and dried over anhydrous sodium sulfate, the solvent was evaporated therefrom and the resulting crystals were recrystallized from chloroform-ethyl acetate-hexane to provide 276 mg (yield 44%) of N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acrylamide as colorless powdery crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. customthe resulting crystals were recrystallized from chloroform-ethyl acetate-hexane

Sources & evidence

ORD record
ord-998637a19c854f8caa205fabc57eb4ba
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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