Chloroform → 2-Bromo-N-(6-methyl-2,4-bis(methylthio)pyridin-3-yl)acetamide

HRID 2219250Notes

Reaction equation

HRID 2219250 reaction equation
C(N(CC)CC)C.C(Cl)(Cl)Cl.[NH2:12][C:13]1[C:14]([S:22][CH3:23])=[N:15][C:16]([CH3:21])=[CH:17][C:18]=1[S:19][CH3:20].[Br:24][CH2:25][C:26](Br)=[O:27]>O>[Br:24][CH2:25][C:26]([NH:12][C:13]1[C:14]([S:22][CH3:23])=[N:15][C:16]([CH3:21])=[CH:17][C:18]=1[S:19][CH3:20])=[O:27]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 99903926-Methyl-2,4-bis-methylsulfanylpyridin-3-ylamine

Product 1

HCID 222471492-Bromo-N-(6-methyl-2,4-bis(methylthio)pyridin-3-yl)acetamideYield 13%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (274 mg, 2.71 mmol) was added to a chloroform (10 ml) solution of 3-amino-2,4-bis(methylthio)-6-methylpyridine (492 mg, 2.46 mmol), and bromoacetyl bromide (521 mg, 2.58 mmol) was then slowly added thereto dropwise while being cooled with ice. The mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with water, and then extracted with methylene chloride. The organic layer was washed with 1N hydrochloric acid, water, an aqueous solution of sodium hydrogencarbonate, water and a saturated aqueous solution of sodium chloride in this order, and dried over sodium sulfate. Subsequently, the solvent was distilled off, and the resulting crude product was purified through silica gel chromatography (silica gel 25 g, eluent—hexane:acetone=7:1→5:1→3:1) to obtain 100 mg (yield 13%) of 2-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide as a colorless crystal (melting point: 171 to 172° C.).

Workup

  1. additionwas then slowly added
  2. temperaturedropwise while being cooled with ice
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with 1N hydrochloric acid, water
  5. dry with materialan aqueous solution of sodium hydrogencarbonate, water and a saturated aqueous solution of sodium chloride in this order, and dried over sodium sulfate
  6. distillationSubsequently, the solvent was distilled off
  7. customthe resulting crude product was purified through silica gel chromatography (silica gel 25 g, eluent—hexane:acetone=7:1→5:1→3:1)

Sources & evidence

ORD record
ord-a138763bfd45462e8ccaf49fb6b146cd
Source dataset
uspto-grants-2008_08
Patent number
US07414066B2

Reaction notes

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