Acetone → Undec-10-enoyl isocyanate

HRID 1907041Notes

Reaction equation

HRID 1907041 reaction equation
O.[N-:2]=[N+]=[N-].[Na+].[C:6](Cl)(=[O:17])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16].C[C:20](C)=[O:21]>>[C:6]([N:2]=[C:20]=[O:21])(=[O:17])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16]

Participants

5

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 33557Sodium AzideHCID 3804210-Undecenoyl chloride

Product 1

HCID 71362130Undec-10-enoyl isocyanate

Procedure

150 g of purified water was added to 45.5 g of sodium azide and a completely homogeneous solution was prepared by stirring while cooling with ice water. To this was added dropwise in small portions a solution prepared by mixing 101.4 g of 10-undecenoyl chloride with 150 mL of acetone; this addition was carried out so as to keep the solution temperature in the range from 10 to 15° C. Stirring at around 12° C. was continued for 1 hour after the completion of addition. The solution was then transferred to a separatory funnel and the aqueous and organic layers were separated. The organic layer was slowly added to 500 mL of toluene held at 60° C., followed by stirring for 3 hours in the temperature range from 50 to 60° C. The toluene was distilled off and distillation in vacuo was thereafter carried out to obtain 73.2 g of 10-undecenoyl isocyanate.

Workup

  1. customa completely homogeneous solution was prepared
  2. additionTo this was added dropwise in small portions a solution
  3. customprepared
  4. additionthis addition
  5. customfrom 10 to 15° C
  6. stirringStirring at around 12° C.
  7. additionafter the completion of addition
  8. customThe solution was then transferred to a separatory funnel
  9. customthe aqueous and organic layers were separated
  10. additionThe organic layer was slowly added to 500 mL of toluene
  11. customheld at 60° C.
  12. stirringby stirring for 3 hours in the temperature range from 50 to 60° C
  13. distillationThe toluene was distilled off
  14. distillationdistillation in vacuo

Sources & evidence

ORD record
ord-863af31c128142319ae85d451c3bb0a8
Source dataset
uspto-grants-2013_12
Patent number
US08597619B2

Reaction notes

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