Hydrochloric Acid → HCID 86642481, compound

HRID 1689747

Reaction equation

HRID 1689747 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7](Cl)[C:3]=1[CH:4]=[N:5][OH:6].[Cl:12]N1C(=O)CCC1=O.[ClH:20]>CN(C=O)C>[Cl:20][O:6][N:5]=[CH:4][C:3]1[CH:7]=[C:8]([Cl:12])[CH:9]=[CH:10][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31398ChlorosuccinimideHCID 91328Benzaldehyde, 2,6-dichloro-, oxime

Product 1

HCID 86642481HCID 86642481, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-Dichloro-benzaldehyde oxime (7.6 g, 40 mmol) is dissolved in 56 mL of DMF and N-chlorosuccinimide (5.9 g, 44.0 mmol) is added followed by a catalytic amount of HCl gas. The reaction mixture is stirred overnight. The reaction mixture is partitioned between ether and water. The layers are separated and the ether layer is washed with brine and is dried over sodium sulfate. The ether layer is filtered and the solvent is removed under reduced pressure to yield the crude product. The crude product is purified via chromatography using a gradient of 10% ethyl acetate in hexanes to 15% ethyl acetate in hexanes to yield the title compound. 1H-NMR (400 MHz, CDCl3) δ 8.76 (broad, 1H), 7.38-7.26 (m, 3H)

Workup

  1. customThe reaction mixture is partitioned between ether and water
  2. customThe layers are separated
  3. washthe ether layer is washed with brine
  4. dry with materialis dried over sodium sulfate
  5. filtrationThe ether layer is filtered
  6. customthe solvent is removed under reduced pressure
  7. customto yield the crude product
  8. customThe crude product is purified via chromatography

Sources & evidence

ORD record
ord-4e199cffcfd24866a61c24e7a6bf75cf
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Linked notes

Loading…