Hydrochloric Acid → HCID 131716713, compound

HRID 1073886Notes

Reaction equation

HRID 1073886 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH:7]([C:16]([CH3:26])([S:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)[CH3:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N+:10]=1[O-:15].Cl>N1C=CC=CC=1>[CH3:1][S:2]([OH:4])(=[O:6])=[O:3].[CH3:1][S:2]([O:6][CH:7]([C:16]([CH3:26])([S:18][C:19]1[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=1)[CH3:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N+:10]=1[O-:15])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chloride2×HCID 131716715HCID 131716715, compound

Product 1

HCID 131716713HCID 131716713, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

1.25 g of methanesulphonyl chloride were added dropwise at 20° C. to a stirred solution of 2.73 g of 2-[2-hydroxy-3-methyl-3-(4-methylthiophenoxy)butyl]pyridine N-oxide in 10 ml of pyridine and the mixture was stirred at 20° C. for 16 hours. A further 1.25 g of methanesulphonyl chloride were then added and the stirring was continued for 3 hours. The mixture was then poured into 2M hydrochloric acid and extracted with ethyl acetate. The solvent was removed by evaporation and the residue was crystallized from ethyl acetate to give 0.95 g of 2-[2-methanesulphonyloxy-3-methyl-3-(4-methylthiophenoxy)butyl]pyridine N-oxide methanesulphonic acid salt in the form of a white solid of melting point 126-128° C.

Workup

  1. waitthe stirring was continued for 3 hours
  2. extractionextracted with ethyl acetate
  3. customThe solvent was removed by evaporation
  4. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-4859283e84b44a3080b7e24b8985cb91
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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