Acetone → 143212-17-3

HRID 1683397Notes

Reaction equation

HRID 1683397 reaction equation
[Cl-].[CH:2]1([CH2:7][CH2:8]C(Cl)=O)[CH2:6][CH2:5][CH2:4][CH2:3]1.[N-:12]=[N+]=[N-].[Na+].C[C:17](C)=[O:18]>O>[CH:2]1([CH2:7][CH2:8][N:12]=[C:17]=[O:18])[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 312ChlorideHCID 33557Sodium AzideHCID 660393-Cyclopentylpropionyl chloride

Product 1

HCID 19043559143212-17-3

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure is an adaptation of procedure in Org. Syn. Col. Vol II, p 846, Col. VI, p 95. A solution of 0.65 g of 3-cyclopentylpropionyl chloride (Example 253) in 10 ml of acetone is added dropwise to a 0° C. solution of 0.46 g of sodium azide in 5 ml of water When the addition is complete, stirring is continued for 1 hour. The mixture is extracted wink toluene, dried over anhydrous sodium sulfate and filtered. The toluene solution is added dropwise to 25 ml of toluene which is heated at reflux temperature. When the addition is complete, the reaction is refluxed until nitrogen evolution has ceased (ca 1 hour). The reaction is cooled and the resulting toluene solution of the corresponding isocyanate is then used a% in Example 124, 119, 99, and all new examples.

Workup

  1. additionthe addition
  2. extractionThe mixture is extracted
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. additionThe toluene solution is added dropwise to 25 ml of toluene which
  6. temperatureis heated
  7. temperatureat reflux temperature
  8. additionWhen the addition
  9. temperaturethe reaction is refluxed until nitrogen evolution
  10. custom(ca 1 hour)
  11. temperatureThe reaction is cooled

Sources & evidence

ORD record
ord-bc6b5808493b4fef9b5325b9714ec183
Source dataset
uspto-grants-1997_06
Patent number
US05637731

Reaction notes

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