Methanesulfonyl chloride → HCID 86744355, compound

HRID 892549Notes

Reaction equation

HRID 892549 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([C:8]1[CH:28]=[CH:27][C:11]([O:12][C:13]([CH3:26])([CH3:25])[CH:14]([OH:24])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N+:17]=2[O-:23])=[CH:10][CH:9]=1)#[N:7]>C(N(CC)CC)C.ClCCl>[C:6]([C:8]1[CH:9]=[CH:10][C:11]([O:12][C:13]([CH3:26])([CH3:25])[CH:14]([O:24][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N+:17]=2[O-:23])=[CH:27][CH:28]=1)#[N:7]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 54509110HCID 54509110, compound

Product 1

HCID 86744355HCID 86744355, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

573 mg of methanesulphonyl chloride were added to a stirred solution of 1.56 g of 2-[3-(4-cyanophenoxy)-2-hydroxy-3-methylbutyl]-6-methylpyridine N-oxide in 3 ml of triethylamine and 25 ml of dichloromethane at room temperature. After 1 hour a further 573 mg of methanesulphonyl chloride were added and the mixture was stirred until thin-layer chromatography indicated that the reaction was complete. The mixture was washed with dilute hydrochloric acid and 2M sodium hydroxide solution, dried over sodium sulphate and evaporated to give 1.8 g of 2-[3-(4-cyanophenoxy)-2-methanesulphonyloxy-3-methylbutyl]-6methylpyridine N-oxide.

Workup

  1. washThe mixture was washed with dilute hydrochloric acid and 2M sodium hydroxide solution
  2. dry with materialdried over sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-77e09d418cce4b92a227248688cbe3f5
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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