2,6-Lutidine → O-(3-chloropropyl)-alpha-chloro-2,6-dichlorobenzaldoxime

HRID 1703739Notes

Reaction equation

CC1C=CC=C(C)N=1.[Cl:9][C:10](=[N:19][OH:20])[C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:18].[Cl:21][CH2:22][CH2:23][CH2:24]S(Cl)(=O)=O>C1C=CC=CC=1>[Cl:21][CH2:22][CH2:23][CH2:24][O:20][N:19]=[C:10]([Cl:9])[C:11]1[C:12]([Cl:18])=[CH:13][CH:14]=[CH:15][C:16]=1[Cl:17]

Participants

Conditions

Temperature: 25 °C

Procedure

A 3.6 g (0.034 mol) sample of 2,6-dimethylpyridine was added dropwise to a cooled solution (ice bath) of 7.4 g (0.033 mol) alpha-chloro-2,6-dichlorobenzaldoxime and 5.9 g (0.03 mol) 3-chloropropylsulfonyl chloride in 75 ml benzene. The reaction mixture was allowed to warm to 25° C., stirred for 2 hours (a red solid formed) and allowed to stand overnight. The reaction mixture was evaporated under reduced pressure and the residue was chromatographed through a silica gel column with dichloromethane. A semi-crystalline yellow product was eluted from the column. The product was recrystallized from ether/hexane to give 4.3 g of O-(3-chloropropyl)-alpha-chloro-2,6-dichlorobenzaldoxime as a white solid, m.p. 69°-71° C. Elemental analysis for C10H9Cl4NO3S showed: %S, calc. 8.8, found 9.2; %Cl, calc. 38.8, found 37.9.

Workup

customformed) and
waitto stand overnight
customThe reaction mixture was evaporated under reduced pressure
customthe residue was chromatographed through a silica gel column with dichloromethane
washA semi-crystalline yellow product was eluted from the column
customThe product was recrystallized from ether/hexane

Sources & evidence

ORD record: ord-c23a0d10e6ef4eec94ad693d80cf5fa1
Source dataset: uspto-grants-1978_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04125397

Reaction notes

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