Dichloromethane → HCID 86605571, compound

HRID 1453956Notes

Reaction equation

HRID 1453956 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[CH2:10][CH2:11][C:12]1[C:13]([N+:18]([O-:20])=[O:19])=[N:14][CH:15]=[CH:16][CH:17]=1)(=O)=O.C(=O)(O)[O-].[Na+].C(Cl)Cl>CS(C)=O>[N:1]([CH2:10][CH2:11][C:12]1[C:13]([N+:18]([O-:20])=[O:19])=[N:14][CH:15]=[CH:16][CH:17]=1)=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 86605570HCID 86605570, compound

Product 1

HCID 86605571HCID 86605571, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

Sodium azide (1.16 g, 17.8 mmol) was added to a solution of 3-(2-methansulfonyloxyethyl)-2-nitropyridine (0.44 g, 1.78 mmol) in dimethyl sulfoxide (5 mL), then stirred overnight at 50° C. The reaction was cooled and worked up with saturated sodium bicarbonate and methylene chloride. The organic phase was dried over sodium sulfate. This material was chromatographed (silica gel, 0-50% ethyl acetate in hexane, gradient elution) to produce the title compound (0.190 g) as a yellow oil. MS 194 (M+1).

Workup

  1. temperatureThe reaction was cooled
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customThis material was chromatographed
  4. wash(silica gel, 0-50% ethyl acetate in hexane, gradient elution)

Sources & evidence

ORD record
ord-4e516c3b03904343851c3432a35c89ce
Source dataset
uspto-grants-2009_01
Patent number
US07476665B2

Reaction notes

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