2,6-Lutidine → HCID 54352845, compound

HRID 1073942Notes

Reaction equation

HRID 1073942 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:21][CH:22]([OH:35])[C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=2)([CH3:25])[CH3:24])=[N+:18]([O-:20])[CH:19]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.N1C(C)=CC=CC=1C>ClCCl>[CH2:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:21][CH:22]([O:35][S:2]([CH3:1])(=[O:4])=[O:3])[C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=2)([CH3:25])[CH3:24])=[N+:18]([O-:20])[CH:19]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 79372,6-Lutidine3×HCID 31297Methanesulfonyl chloride3×HCID 545624775-benzyloxy-2-[3-(4-cyanophenoxy)-2-hydroxy-3-methylbutyl]pyridine N-oxide

Product 1

HCID 54352845HCID 54352845, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.7 g of methanesulphonyl chloride was added to a stirred solution of 2.3 g of 5-benzyloxy-2-[3-(4-cyanophenoxy)-2-hydroxy -3-methylbutyl]pyridine N-oxide and 1 ml of 2,6-lutidine in 10 ml of dichloromethane. The mixture was stirred for 4.5 hours and then a further 1 ml of 2,6-lutidine and 0.7 g of methanesulphonyl chloride were added. After 2.5 hours a further 1 ml of 2,6-lutidine and 0.7 g of methanesulphonyl chloride were added and the mixture was stirred for 16 hours. The mixture was then diluted with 50 ml of dichloromethane and washed in succession with 2M hydrochloric acid, water and 10% sodium bicarbonate solution The organic solution was evaporated and the residue was chromatographed on silica gel using diethyl ether/methanol (9:1) for the elution to give 0.89 g of 5-benzyloxy-2-[3-(4-cyanophenoxy)-3-methyl-2-(methylsulphonyloxy)butyl]pyridine N-oxide in the form of a cream solid of melting point 142° C. after recrystallization from ethyl acetate.

Workup

  1. stirringthe mixture was stirred for 16 hours
  2. washwashed in succession with 2M hydrochloric acid, water and 10% sodium bicarbonate solution The organic solution
  3. customwas evaporated
  4. customthe residue was chromatographed on silica gel
  5. washfor the elution

Sources & evidence

ORD record
ord-3d673c2e98704bd6b4d7dbe90b5b9057
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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