Sodium Azide → HCID 86590309, compound

HRID 899630Notes

Reaction equation

HRID 899630 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@@H:8](Cl)[CH:7]=[CH:6]1)(=[O:3])[CH3:2].[N-:12]=[N+:13]=[N-:14].[Na+]>CN(C=O)C.[Cl-].[Na+].O.C(OCC)C.O>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([N:12]=[N+:13]=[N-:14])[CH:7]=[CH:6]1)(=[O:3])[CH3:2]

Participants

7

Reactant 2

HCID 33557Sodium AzideHCID 11137633HCID 11137633, compound

Product 1

HCID 86590309HCID 86590309, compoundYield 85.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of cis-1-acetoxy-4-chloro-2-cyclohexene (6.87 g, 39.4 mmol) in DMF (160 mL) was added sodium azide (5.29 g, 81.1 mmol) and the resultant mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into brine (160 mL) and diluted with diethyl ether (300 mL) and water (80 mL). The phases were separated and the organic phase was washed with brine (5×50 mL). The organic phase was dried (MgSO4), and concentrated to provide 6.13 g (85%) of trans-1-acetoxy-4-azido-2-cyclohexene as a pale red oil which was used without further purification.

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with brine (5×50 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4c594f2dd0c3489780462afee5b50bc3
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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