Triethylamine → HCID 22272659, compound

HRID 1064801Notes

Reaction equation

HRID 1064801 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[C:10]([S:15][CH3:16])=[N:11][CH:12]=[CH:13][CH:14]=1.[Br:17][CH2:18][C:19](Br)=[O:20]>C1COCC1.O>[CH3:16][S:15][C:10]1[C:9]([NH:8][C:19](=[O:20])[CH2:18][Br:17])=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 156561362-(Methylsulfanyl)pyridin-3-amine

Product 1

HCID 22272659HCID 22272659, compoundYield 22.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Triethylamine (197 mg, 1.95 mmol) was added to a solution of 3-amino-2-(methylthio)pyridine (248 mg, 1.77 mmol) in THF (5 ml), then a solution of bromoacetyl bromide (428 mg, 2.12 mmol) in THF (1 ml) was dropped thereinto and the mixture was stirred for 17 hours. The reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate, the solvent was evaporated therefrom and the residue was purified by a silica gel column chromatography (developing solvent, hexane:ethyl acetate=5:1) to provide 104 mg (yield 22%) of N-(2-methylthio-3-pyridyl)-2-bromoacetamide as colorless powdery crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. customthe residue was purified by a silica gel column chromatography (developing solvent, hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-91e12dc60c3349379c5464f3a73653f6
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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