Carbon Tetrachloride → HCID 21339854, compound

HRID 2184626Notes

Reaction equation

HRID 2184626 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]([C:16]3[CH:21]=[C:20](C)[CH:19]=[CH:18][C:17]=3[CH3:23])=[N:14][N:15]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:24]N1C(=O)CCC1=O.[C:32]([Cl:36])(Cl)(Cl)Cl>>[Cl:24][CH2:23][C:17]1[CH:18]=[CH:19][C:20]([CH2:32][Cl:36])=[CH:21][C:16]=1[C:13]1[O:12][C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=2)=[N:15][N:14]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 31398ChlorosuccinimideHCID 22457286HCID 22457286, compound

Product 1

HCID 21339854HCID 21339854, compoundYield 42%

Conditions

Temperature
0 °C

Procedure

Compound 3 (3.0 g, 9.79 mmol) and N-chloro-succinimide (3.27 g, 24.48 mmol) were dissolved in carbon tetrachloride (20 ml). The mixture was degassed and heated/irradiated by an IR lamp to reflux under argon. After 4 hours, the mixture was cooled to 0° C. The soluble part of the mixture was separated by filtration. Evaporation of the solvent afforded a solid mixture product, which was separated and purified by silica flash column chromatography using hexane to hexane/EtOAC (1:4, v/v) subsequently. The product was obtained as an off-white powder with a yield of 42%. The compound was characterized by 1H NMR and FT-IR.

Workup

  1. customThe mixture was degassed
  2. customheated/irradiated by an IR lamp
  3. temperatureto reflux under argon
  4. customThe soluble part of the mixture was separated by filtration
  5. customEvaporation of the solvent
  6. customafforded a solid mixture product, which
  7. customwas separated
  8. custompurified by silica flash column chromatography
  9. customThe product was obtained as an off-white powder with a yield of 42%

Sources & evidence

ORD record
ord-54435ef1975544a9af6174664c2acfae
Source dataset
uspto-grants-2002_06
Patent number
US06399224B1

Reaction notes

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