Methyl iodide → HCID 68664211, compound

HRID 452811Notes

Reaction equation

HRID 452811 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]2[CH:13]=[C:14]([C:17]([NH:19][NH2:20])=[O:18])[CH:15]=[CH:16][C:11]=2[O:10][CH:9]=1.C(N(CC)CC)C.[C:28](=[S:30])=S.IC.[C:33](=O)([O-])[O-].[K+].[K+]>C(O)C.C(OCC)(=O)C.CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]2[CH:13]=[C:14]([C:17]3[O:18][C:33]([S:30][CH3:28])=[N:20][N:19]=3)[CH:15]=[CH:16][C:11]=2[O:10][CH:9]=1

Participants

9

Reactant 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 68663792HCID 68663792, compound

Product 1

HCID 68664211HCID 68664211, compoundYield 73.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(2-chlorophenyl)-1-benzofuran-5-carbohydrazide (2.22 g, 7.74 mmol), triethylamine (2.14 mL, 15.4 mmol) and carbon disulfide (6.96 g, 116.1 mmol) in ethanol (25 mL) was heated under reflux overnight. After cooling, iodomethane (0.96 mL, 15.4 mmol), potassium carbonate (1.60 g, 11.6 mmol) and N,N-dimethylformamide (25 mL) were added to the reaction mixture, and the resulting mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1) and recrystallized from hexane/ethyl acetate to give the title compound (1.95 g, yield 73%) as colorless crystals.

Workup

  1. temperatureunder reflux overnight
  2. temperatureAfter cooling
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1)
  7. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-aa8f3faaceaf4e76ba6b649b4b076ed3
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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