Dichloromethane → Methanesulfonyl azide, trifluoro-

HRID 1844293Notes

Reaction equation

HRID 1844293 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].C(Cl)Cl.[O:8](S(C(F)(F)F)(=O)=O)[S:9]([C:12]([F:15])([F:14])[F:13])(=O)=[O:10]>O>[S:9]([N:1]=[N+:2]=[N-:3])([C:12]([F:15])([F:14])[F:13])(=[O:10])=[O:8]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 10986786Methanesulfonyl azide, trifluoro-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of NaN3 (3445 mg, 53 mmol) in H2O (12 mL) was added CH2Cl2 (18 mL). The resulting biphasic mixture was cooled in an ice bath and stirred vigorously and treated with Tf2O (3000 mg, 106 mmol) over a period of 60 min. The reaction mixture was stirred in an ice bath for 4 h. The organic phase was separated and the aqueous phase was extracted once with CH2Cl2 (20 mL). The organic extracts were washed with saturated Na2CO3 solution and used without further purification.

Workup

  1. temperatureThe resulting biphasic mixture was cooled in an ice bath
  2. stirringThe reaction mixture was stirred in an ice bath for 4 h
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted once with CH2Cl2 (20 mL)
  5. washThe organic extracts were washed with saturated Na2CO3 solution
  6. customused without further purification

Sources & evidence

ORD record
ord-fa11e1bb5410490cb7f62170cc87250a
Source dataset
uspto-grants-2015_02
Patent number
US08946391B2

Reaction notes

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