Water → 3-Chloro-2-methyl-6-methylsulfonylbenzaldoxime

HRID 397150Notes

Reaction equation

HRID 397150 reaction equation
[N:1](OCCCC)=[O:2].[CH3:8][C:9]1[C:14]([CH3:15])=[C:13]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[CH:11][C:10]=1[Cl:20].CC(C)([O-])C.[K+].O>CN(C)C=O.C(O)(=O)C>[Cl:20][C:10]1[C:9]([CH3:8])=[C:14]([C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:12][CH:11]=1)[CH:15]=[N:1][OH:2]

Participants

7

Reactant 4

HCID 962WaterHCID 10996Butyl nitriteHCID 18757270HCID 18757270, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 734619433-Chloro-2-methyl-6-methylsulfonylbenzaldoxime

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 12.7 g (119 mmol) of n-butyl nitrite (97%) and 20 g (92 mmol) of 2,3-dimethyl-4-methylsulfonylchlorobenzene in 100 ml of dimethylformamide is cooled to from −55 to −60° C., and a solution of 16.8 g (147 mmol) of potassium tert-butoxide in 70 ml of dimethylformamide is added dropwise at this temperature, over a period of 30 minutes. The reaction is monitored by HPLC. For work-up, initially 50 ml of water are added, and the mixture is then adjusted to pH 5-6 using about 30 ml of glacial acetic acid. The mixture is then poured onto 0.7 kg of ice-water and the aqueous phase is extracted with methylene chloride. The organic phase is washed with sodium bicarbonate solution, dried over magnesium sulfate and concentrated. This gives 18.4 g of a light-beige crude product which is purified by recrystallization from about 30 ml of toluene.

Workup

  1. extractionthe aqueous phase is extracted with methylene chloride
  2. washThe organic phase is washed with sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThis gives 18.4 g of a light-beige crude product which is purified by recrystallization from about 30 ml of toluene

Sources & evidence

ORD record
ord-60e505f5e64b43b995644c756b19a177
Source dataset
uspto-grants-2003_08
Patent number
US06608209B2

Reaction notes

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