Tetrahydrofuran → 4-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]butanamide

HRID 746642Notes

Reaction equation

HRID 746642 reaction equation
C(N(CC)CC)C.C1COCC1.[NH2:13][C:14]1[C:15]([S:23][CH3:24])=[N:16][C:17]([CH3:22])=[CH:18][C:19]=1[S:20][CH3:21].[Br:25][CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30]>O>[Br:25][CH2:26][CH2:27][CH2:28][C:29]([NH:13][C:14]1[C:15]([S:23][CH3:24])=[N:16][C:17]([CH3:22])=[CH:18][C:19]=1[S:20][CH3:21])=[O:30]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 702254-Bromobutyryl chlorideHCID 99903926-Methyl-2,4-bis-methylsulfanylpyridin-3-ylamine

Product 1

HCID 225921434-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]butanamideYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (206 mg, 2.04 mmol) was added to a THF (6 ml) solution of 3-amino-2,4-bis(methylthio)-6-methylpyridine (341 mg, 1.70 mmol), and 4-bromobutanoyl chloride (379 mg, 2.04 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 ethyl acetate. The organic layer was washed with water and then with a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. Subsequently, the solvent was distilled off, and the resulting crude product was purified through silica gel chromatography (silica gel 75 g, eluent—hexane:acetone=5:1→3:1) to obtain 390 mg (yield 66%) of 4-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]butanamide as a colorless crystal (melting point: 139 to 140° C.).

Workup

  1. additionwas then slowly added
  2. temperaturedropwise while being cooled with ice
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialwith a saturated aqueous solution of sodium chloride, 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 75 g, eluent—hexane:acetone=5:1→3:1)

Sources & evidence

ORD record
ord-304e0786b76d4c8c8a5df511623447a6
Source dataset
uspto-grants-2008_07
Patent number
US07393866B2

Reaction notes

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