Water → HCID 22061606, compound

HRID 2104307Notes

Reaction equation

HRID 2104307 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].O.[F:6][C:7]([F:35])([CH2:30][CH2:31][C:32](Cl)=[O:33])[C:8]([F:29])([F:28])[C:9]([F:27])([F:26])[C:10]([F:25])([F:24])[C:11]([F:23])([F:22])[C:12]([F:21])([F:20])[C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15].COC>CC(C)=O>[F:6][C:7]([F:35])([CH2:30][CH2:31][C:32]([N:1]=[N+:2]=[N-:3])=[O:33])[C:8]([F:28])([F:29])[C:9]([F:26])([F:27])[C:10]([F:25])([F:24])[C:11]([F:22])([F:23])[C:12]([F:21])([F:20])[C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15]

Participants

6

Reactant 4

HCID 962Water2×HCID 8254Dimethyl EtherHCID 33557Sodium Azide2×HCID 10864135(Perfluorooctyl)propanoyl chloride

Product 1

HCID 22061606HCID 22061606, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium azide (6.0 g) was put in a 250 mL round-bottom flask (2-neck) equipped with a thermometer. H2O (20 mL) was added to dissolve sodium azide. It was cooled on an ice-water bath. A solution of 3-(perfluorooctyl)propionyl chloride (12.9 g) in acetone (25 mL) was added dropwise to keep the temperature below 12° C. The mixture was vigorously stirred for 2 h. Dimethyl ether (100 mL) and water (100 mL) are added, and the mixture was vigorously stirred for 1 min. After the separation of two layers, the aqueous layer was extracted with ether (2×50 mL). The ether layers were combined, and are washed with water (3×100 mL) and brine. After drying over MgSO4, the solvent was removed under vacuum to give a mixture of white solid and liquid (12.0 g) that was immediately used for the next reaction.

Workup

  1. custom(2-neck) equipped with a thermometer
  2. temperatureIt was cooled on an ice-water bath
  3. customthe temperature below 12° C
  4. stirringthe mixture was vigorously stirred for 1 min
  5. customAfter the separation of two layers
  6. extractionthe aqueous layer was extracted with ether (2×50 mL)
  7. washare washed with water (3×100 mL) and brine
  8. dry with materialAfter drying over MgSO4
  9. customthe solvent was removed under vacuum
  10. customto give
  11. customwas immediately used for the next reaction

Sources & evidence

ORD record
ord-c57d6cdc6c22450c8d9c0fc5112622f0
Source dataset
uspto-grants-2009_08
Patent number
US07576245B2

Reaction notes

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