Chloromethyl methyl sulfide → HCID 68664412, compound

HRID 452784Notes

Reaction equation

HRID 452784 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]4[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=4)[C:11]=3[CH:22]=2)=[N:4][N:3]=1.[H-].[Na+].[CH3:25][S:26][CH2:27]Cl>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]4[CH:16]=[CH:17][C:18]([O:21][CH2:25][S:26][CH3:27])=[CH:19][CH:20]=4)[C:11]=3[CH:22]=2)=[N:4][N:3]=1

Participants

6

Reactant 3

HCID 16916Chloromethyl methyl sulfideHCID 24758Sodium hydrideHCID 444820244-[5-(5-Methyl-1,3,4-oxadiazol-2-yl)-1-benzofuran-3-yl]phenol

Product 1

HCID 68664412HCID 68664412, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-1-benzofuran-3-yl]phenol (1.17 g, 4.00 mmol) in N,N-dimethylformamide (15 mL) was added sodium hydride (60% in oil, 0.320 g, 8.00 mmol) at room temperature, and the resulting mixture was stirred for 15 min. (Chloromethyl) methyl sulfide (90%, 0.744 mL, 8.00 mmol) was added to the reaction mixture, and the resulting mixture was further stirred for 1 hr. The reaction mixture was diluted with ethyl acetate, washed twice with water and once with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=2/1) and recrystallized from methanol to give the title compound (1.22 g, yield 87%) as colorless crystals.

Workup

  1. additionwas added to the reaction mixture
  2. washwashed twice with water and once with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=2/1)
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-074b2cb7c8974fb8857e2306a10e050e
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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