Pyridine → HCID 86669076, compound

HRID 1807402Notes

Reaction equation

HRID 1807402 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:14])=[C:5]([Cl:13])[C:6]=1[C@@H:7]1[CH2:9][C@H:8]1[C:10](=O)[CH3:11].N1C=CC=CC=1.Cl.[CH3:22][O:23][NH2:24]>CO.O>[CH3:22][O:23][N:24]=[C:10]([C@@H:8]1[CH2:9][C@H:7]1[C:6]1[C:5]([Cl:13])=[C:4]([Cl:14])[S:3][C:2]=1[Cl:1])[CH3:11]

Participants

6

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 67086633HCID 67086633, compound

Product 1

HCID 86669076HCID 86669076, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of trans 1-[2-(2,4,5-trichloro-thiophen-3-yl)-cyclopropyl]-ethanone (2.7 g; 10 mmol) prepared as described in example P29, in methanol (20 ml) at ambient temperature was added pyridine (1.25 ml; 15 mmol) and methoxyamine hydrochloride (1.3 g; 15 mmol). The reaction mixture was stirred for 4 hours at ambient temperature then poured in water (50 ml) and extracted with dichloromethane (3×30 ml). Combined organic layers were washed with water (30 ml) and dried over anhydrous sodium sulphate. The solvent was removed in vacuo to afford 2.85 g (95% of theory) of trans 1-[2-(2,4,5-trichloro-thiophen-3-yl)-cyclopropyl]-ethanone O-methyl-oxime as an E/Z mixture in form of an orange oil.

Workup

  1. extractionextracted with dichloromethane (3×30 ml)
  2. washCombined organic layers were washed with water (30 ml)
  3. dry with materialdried over anhydrous sodium sulphate
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-849cfcd667ee4fff9ddd86eeabf918ed
Source dataset
uspto-grants-2013_01
Patent number
US08357635B2

Reaction notes

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