Sodium Chloride → HCID 10635673, compound

HRID 355548Notes

Reaction equation

HRID 355548 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([CH2:11][CH2:12][C@H:13]([OH:27])[CH2:14]OS(CC2C=CC(C)=CC=2)(=O)=O)=[CH:9][CH:10]=1)=[O:5])[CH3:2].[N-:28]=[N+:29]=[N-:30].[Na+].[Na+].[Cl-]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([CH2:11][CH2:12][C@H:13]([OH:27])[CH2:14][N:28]=[N+:29]=[N-:30])=[CH:9][CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 33557Sodium AzideHCID 53940941HCID 53940941, compound

Product 1

HCID 10635673HCID 10635673, compoundYield 113.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 42.94 g (108 mmol) of the tosylate (4) in 250 ml of DMF (N,N-dimethylformamide) was added 31.52 g (485 mmol) of sodium azide. The solution was heated under argon for 4 hours at 80° C. The reaction mixture was cooled and poured into 600 ml of saturated NaCl, and the resulting oil was separated. The aqueous solution was extracted three times with Et2O. The Et2O extracts were combined with the oil and washed once with saturated NaCl, dried (MgSO4), and concentrated, yielding 33.0 g of the azide (5) as a crude product that was sufficiently pure to use in the next step (f). An analytical sample of the azide (5) was obtained by flash chromatography on silica gel, eluting CH2Cl2 -EtOAc (20:1) to produce a colorless oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe resulting oil was separated
  3. extractionThe aqueous solution was extracted three times with Et2O
  4. washwashed once with saturated NaCl
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-300024e2e2f14e8c8b44a5aacd70dfec
Source dataset
uspto-grants-1998_11
Patent number
US05831100

Reaction notes

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