Sodium Azide → HCID 57722716, compound

HRID 1987068Notes

Reaction equation

HRID 1987068 reaction equation
[F:1][C:2]([F:16])([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=1)[CH2:3]OS(C)(=O)=O.[N-:17]=[N+:18]=[N-:19].[Na+]>CS(C)=O>[N:17]([CH2:3][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=1)([F:16])[F:1])=[N+:18]=[N-:19]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 57722725HCID 57722725, compound

Product 1

HCID 57722716HCID 57722716, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
180 °C

Procedure

Methanesulfonic acid 2,2-difluoro-2-(6-methyl-pyridin-2-yl)-ethyl ester (900 mg, 3.83 mmol), as prepared in the preceding step, was dissolved in DMSO (2 mL). To this solution was added sodium azide (498 mg, 7.65 mmol) and the reaction mixture was heated at 180° C. under microwave irradiation for 1 hour. The reaction mixture was partitioned between water and ethyl acetate. The combined ethyl acetate extracts were dried over Na2SO4 and concentrated to afford a brown residue (700 mg, 92%). 1H NMR (CDCl3) δ 7.73 (t, J=7.82 Hz, 1H), 7.52 (d, J=7.76 Hz, 1H), 7.26 (d, J=7.79 Hz, 1H), 4.02 (t, J=13.23 Hz, 2H), 2.50 (s, 3H).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. dry with materialThe combined ethyl acetate extracts were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e1a53ebb80c74b1db30774675d51392d
Source dataset
uspto-grants-2009_06
Patent number
US07550474B2

Reaction notes

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