Sodium methanethiolate → HCID 68958420, compound

HRID 2378057Notes

Reaction equation

HRID 2378057 reaction equation
[CH3:1][S-:2].[Na+].[CH3:4][O:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:17]([C:25]3([CH2:28]OS(C)(=O)=O)[CH2:27][CH2:26]3)[O:16][N:15]=2)=[CH:10][CH:9]=1>CN(C)C=O.C(OCC)(=O)C>[CH3:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[C:18]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[C:17]([C:25]3([CH2:28][S:2][CH3:1])[CH2:26][CH2:27]3)[O:16][N:15]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 86613311HCID 86613311, compound

Product 1

HCID 68958420HCID 68958420, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture consisting of sodium thiomethoxide (0.33 g) in N,N-dimethylformamide (3 mL) is added a mixture consisting of methanesulfonic acid 1-[3-(4-methoxymethoxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropylmethyl ester (synthetic intermediate prepared in Example 11, Step iv, 1 g) in N,N-dimethylformamide at 0° C. The mixture is stirred at 80° C. for four hours and is cooled to room temperature. The mixture is then diluted with ethyl acetate (50 mL) and is sequentially washed with 1 N hydrochloric acid solution (3×15 mL), water (15 mL), and brine solution (15 mL.) The mixture is dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford the synthetic intermediate 3-(4-methoxymethoxy-phenyl)-5-(1-methylsulfanylmethyl-cyclopropyl)-4-phenyl-isoxazole (0.89 g.)

Workup

  1. additionis added a mixture
  2. temperatureis cooled to room temperature
  3. washis sequentially washed with 1 N hydrochloric acid solution (3×15 mL), water (15 mL), and brine solution (15 mL.) The mixture
  4. dry with materialis dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c8c18aa6cf19477ea7866815f470b37b
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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