Sodium Azide → HCID 178451158, compound

HRID 271358Notes

Reaction equation

HRID 271358 reaction equation
CS(O[CH2:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14])[CH2:9][CH2:8]1)(=O)=O.[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C)C=O>[N:20]([CH2:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14])[CH2:9][CH2:8]1)=[N+:21]=[N-:22]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 178451163HCID 178451163, compound

Product 1

HCID 178451158HCID 178451158, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of crude butyl cis-4-{[(methylsulfonyl)oxy]methyl}-cyclohexane carboxylate (35.3 g, 117 mmol) in dimethylformamide (146 ml) was added sodium azide (30.4 g, 468 mmol, 4 equiv.). The mixture was stirred under nitrogen at 80° C. for eight hours. Approximately one-half of the dimethylformamide was distilled off (80° C. oil bath, 3.5 mm). The residue was diluted with water (750 ml) and extracted with ether (3×250 ml). The combined extract was washed with water (2×100 ml) and brine (100 ml), dried (sodium sulfate), filtered, and the solvent was evaporated under reduced pressure to give crude butyl cis-4-(azidomethyl)cyclohexanecarboxylate (26.80 g, 98%) as a yellow oil.

Workup

  1. distillationApproximately one-half of the dimethylformamide was distilled off (80° C. oil bath, 3.5 mm)
  2. additionThe residue was diluted with water (750 ml)
  3. extractionextracted with ether (3×250 ml)
  4. extractionThe combined extract
  5. washwas washed with water (2×100 ml) and brine (100 ml)
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1c50ea9fe7664daf9c10ba1373bdfa45
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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