Ethylene → HCID 11333689, compound

HRID 2084620Notes

Reaction equation

HRID 2084620 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([C:8]([Cl:11])=[CH:9][CH:10]=1)[CH:5]=[N:6][OH:7].[CH2:13]=[CH2:14].[O-]Cl.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([C:5]2[CH2:14][CH2:13][O:7][N:6]=2)[C:8]([Cl:11])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6325EthyleneHCID 23665760Sodium HypochloriteHCID 72770457HCID 72770457, compound

Product 1

HCID 11333689HCID 11333689, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a pressure container, 50 g (0.25 mol) of 3,6-dichloro-2-methylbenzaldoxime are dissolved in 750 ml of methylene chloride. 16 g of ethylene are applied, and 620 g of a 12.5% strength solution of NaOCl are then pumped in at room temperature, and the mixture is stirred overnight. The pressure vessel is vented, and the organic phase is then separated off, washed once with water and dried, and the solvent is removed under reduced pressure. This gives 58 g of product (95% pure) (95% of theory). 1H-NMR (DMSO-D6): 2.3 ppm (s, 3H, Me), 3.3 ppm (t, 2H, CH2), 4.5 ppm (t, 2H, CH2), 7.45 ppm (d, 1H, arom-H), 7.6 ppm (d, 1H, arom-H).

Workup

  1. customare then pumped in at room temperature
  2. customthe organic phase is then separated off
  3. washwashed once with water
  4. customdried
  5. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-656bda6098a64ab184d2b5d7f0233937
Source dataset
uspto-grants-2004_04
Patent number
US06716989B2

Reaction notes

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