Sodium Hydroxide → Azacycloundecan-2-one

HRID 2054563

Reaction equation

HRID 2054563 reaction equation
[C:1]1(=[O:11])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N-:12]=[N+]=[N-].[Na+].[OH-].[Na+]>S(=O)(=O)(O)O.O>[C:1]1(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:12]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 73918Cyclodecanone

Product 1

HCID 70523Azacycloundecan-2-oneYield 112.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Cyclodecanone (n=6) (1.0 g) in 10 mL concentrated sulfuric acid was cooled to 0° C. and 0.54 g of sodium azide was added. The reaction continued to stir at 0° C. for 1 h and warmed to room temperature where it was stirred for two h. The solution was diluted with cold water and treated with cold 10% NaOH solution until pH=9. Extraction with ether (2×), drying over magnesium sulfate and evaporation of solvent provided 1.23 g of 2-azacycloundecanone.

Workup

  1. temperaturewarmed to room temperature where it
  2. stirringwas stirred for two h
  3. extractionExtraction with ether (2×)
  4. dry with materialdrying over magnesium sulfate and evaporation of solvent

Sources & evidence

ORD record
ord-b94c6932bf0b45b18cd81454ddf177d6
Source dataset
uspto-grants-2008_02
Patent number
US07329683B2

Linked notes

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