Propylene → Propan-2-yl 2-chlorobenzene-1-carboximidate

HRID 1388367Notes

Reaction equation

HRID 1388367 reaction equation
S(F)(=O)(=O)O.C(=O)=O.[CH:9]([OH:12])([CH3:11])[CH3:10].C=CC.[Cl:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([NH2:21])=O.[OH-].[Na+]>C(Cl)Cl>[Cl:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](=[NH:21])[O:12][CH:9]([CH3:11])[CH3:10]

Participants

7

Reactant 5

HCID 8252PropyleneHCID 14798Sodium HydroxideHCID 24603Fluorosulfuric acidHCID 691112-ChlorobenzamideHCID 86586944Isopropanol carbon dioxide

Product 1

HCID 13092606Propan-2-yl 2-chlorobenzene-1-carboximidate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ten grams (0.100 moles) of fluorosulfuric acid is placed in a flask equipped with a dry ice condenser and maintained at -78° (dry ice/isopropanol bath) under an atmosphere of dry nitrogen. To this is added about 25 ml of propylene with moderate stirring giving an orange-colored solution. The reaction mixture is stirred for 15 min. and then diluted with 100 ml of methylene chloride, precooled to -50° C. To this is added at once 15.6 g (0.100 moles) of 2-chlorobenzamide and the mixture stirred at ambient temperature for 18 hrs. giving a deep purple-red solution. The reaction mixture is then poured into 300 ml. of 1 N sodium hydroxide with rapid stirring. After standing briefly the layers are separated. Dilution with saturated sodium chloride solution and methylene chloride facilitates separation of the layers. The turbid organic phase is dried (Na2SO4), filtered through celite filter aid, and the solvent removed in vacuo. The residue is triturated with hexane (Skellysolve B®) and filtered, thereby removing any unreacted 2-chlorobenzamide. The filtrate is distilled under reduced pressure to afford 1-methylethyl 2-chlorobenzenecarboximidate as an oil.

Workup

  1. customequipped with a dry ice condenser
  2. customgiving an orange-colored solution
  3. stirringThe reaction mixture is stirred for 15 min.
  4. customprecooled to -50° C
  5. stirringthe mixture stirred at ambient temperature for 18 hrs
  6. customgiving a deep purple-red solution
  7. additionThe reaction mixture is then poured into 300 ml
  8. customare separated
  9. customseparation of the layers
  10. dry with materialThe turbid organic phase is dried (Na2SO4)
  11. filtrationfiltered through celite
  12. filtrationfilter aid
  13. customthe solvent removed in vacuo
  14. customThe residue is triturated with hexane (Skellysolve B®)
  15. filtrationfiltered
  16. customremoving any unreacted 2-chlorobenzamide
  17. distillationThe filtrate is distilled under reduced pressure

Sources & evidence

ORD record
ord-5995ad8228dc4266868ce04c48013ec5
Source dataset
uspto-grants-1984_02
Patent number
US04431667

Reaction notes

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