Triethylamine → O-isopropylsulfonyl-alpha-chloro-2,6-dichlorobenzaldoxime

HRID 1703738Notes

Reaction equation

HRID 1703738 reaction equation
C(N(CC)CC)C.[Cl:8][C:9](=[N:18][OH:19])[C:10]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:17].[CH:20]([S:23](Cl)(=[O:25])=[O:24])([CH3:22])[CH3:21]>C(OCC)C>[CH:20]([S:23]([O:19][N:18]=[C:9]([Cl:8])[C:10]1[C:11]([Cl:17])=[CH:12][CH:13]=[CH:14][C:15]=1[Cl:16])(=[O:25])=[O:24])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 28001642,6-Dichlorobenzaldchloroxime

Product 1

HCID 54146692O-isopropylsulfonyl-alpha-chloro-2,6-dichlorobenzaldoxime

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 3.6 (0.036 mol) sample of triethylamine was added slowly to a cooled mixture (ice bath) of 7.8 g (0.035 mol) alpha-chloro-2,6-dichlorobenzaldoxime (U.S. Pat. No. 3,234,255) and 5.5 g (0.035 mol) isopropylsulfonyl chloride in 125 ml diethyl ether. The reaction was slightly exothermic. The reaction mixture was filtered to remove a small amount of salts and the filtrate was evaporated under reduced pressure to give a yellow oil. The oil was chromatographed through a silica gel column with hexane/dichloromethane elution. O-isopropylsulfonyl-alpha-chloro-2,6-dichlorobenzaldoxime (white solid, m.p. 48°-50° C.) was eluted from the column with dichloromethane. Elemental analysis for C11H12Cl3NO3S showed: %S, calc. 9.3, found 8.1; %Cl, calc. 30.9, found 32.8.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove a small amount of salts
  3. customthe filtrate was evaporated under reduced pressure
  4. customto give a yellow oil
  5. customThe oil was chromatographed through a silica gel column with hexane/dichloromethane elution
  6. washO-isopropylsulfonyl-alpha-chloro-2,6-dichlorobenzaldoxime (white solid, m.p. 48°-50° C.) was eluted from the column with dichloromethane

Sources & evidence

ORD record
ord-04399c6a160c47369133adac11e5cd22
Source dataset
uspto-grants-1978_11
Patent number
US04125397

Reaction notes

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