Sulfuryl chloride → Methanesulfonic acid 4-chloro-5-(3-chloro-phenyl)-isoxazol-3-ylmethyl ester

HRID 732048Notes

Reaction equation

HRID 732048 reaction equation
S(Cl)([Cl:4])(=O)=O.[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2[O:17][N:16]=[C:15]([CH2:18][O:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:14]=2)[CH:10]=[CH:11][CH:12]=1>ClCCl>[Cl:4][C:14]1[C:15]([CH2:18][O:19][S:20]([CH3:23])(=[O:22])=[O:21])=[N:16][O:17][C:13]=1[C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([Cl:6])[CH:8]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 57838012[5-(3-Chlorophenyl)isoxazol-3-yl]methyl methanesulfonate

Product 1

HCID 86593821Methanesulfonic acid 4-chloro-5-(3-chloro-phenyl)-isoxazol-3-ylmethyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

Sulfuryl chloride (1 ml) was added to methanesulfonic acid 5-(3-chloro-phenyl)-isoxazole-3-ylmethyl ester (200 mg, 0.70 mmol) and then stirred at 60° C. overnight. The reaction mixture was diluted with dichloromethane, washed saturated sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and concentrated to afford methanesulfonic acid 4-chloro-5-(3-chloro-phenyl)-isoxazol-3-ylmethyl ester (219 mg, 97%, light brown solid). 1H NMR (CDCl3) d (ppm): 8.07 (m, 1H), 7.92 (m, 1H), 7.50 (m, 2H), 5.38 (s, 2H), 3.16 (s, 3H).

Workup

  1. washwashed saturated sodium bicarbonate
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-71fed092bb80407489301405a132bee8
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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