Sodium Azide → HCID 59532362, compound

HRID 2193456Notes

Reaction equation

HRID 2193456 reaction equation
CS(O[CH2:6][CH2:7][C:8]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:13][C:12](=[O:14])[N:11]([C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[F:28])[CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)(=O)=O.[N-:35]=[N+:36]=[N-:37].[Na+]>CN(C=O)C.CCOC(C)=O.O>[N:35]([CH2:6][CH2:7][C:8]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:13][C:12](=[O:14])[N:11]([C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[F:28])[CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[N+:36]=[N-:37]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 59532363HCID 59532363, compound

Product 1

HCID 59532362HCID 59532362, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-(3-(2′,4′-difluorobiphenyl-3-yl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)ethyl methanesulfonate (230 mg, 0.47 mmol) in anhydrous DMF (5 mL) was added NaN3 (92 mg, 1.42 mmol). The reaction mixture was heated to 70° C. overnight. The reaction mixture was cooled to rt and diluted with EtOAc (30 mL), and water (20 ml). The organic phase was washed with water (3×20 mL), dried over Na2SO4 and evaporated to give 6-(2-azidoethyl)-3-(2′,4′-difluorobiphenyl-3-yl)-6-phenyl-1,3-oxazinan-2-one (100 mg, 49%).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. washThe organic phase was washed with water (3×20 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-d0aa8a2f2a24422fa93887c1f98bd7bc
Source dataset
uspto-grants-2012_12
Patent number
US08329897B2

Reaction notes

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