Dimethylformamide → HCID 86642386, compound

HRID 426042Notes

Reaction equation

HRID 426042 reaction equation
CS(O[CH2:6][CH2:7][O:8][CH:9]([C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[CH3:28])[CH2:10][CH2:11][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH3:13])(=O)=O.CN(C=O)C.[N-:34]=[N+:35]=[N-:36].[Na+]>C(OCC)(=O)C>[N:34]([CH2:6][CH2:7][O:8][CH:9]([C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[CH3:28])[CH2:10][CH2:11][N:12]([CH3:13])[C:14](=[O:15])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N+:35]=[N-:36]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 86642387HCID 86642387, compound

Product 1

HCID 86642386HCID 86642386, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

2-(3-(tert-Butoxycarbonyl(methyl)amino)-1-(5-chloro-2-methylphenyl)propoxy)ethyl methanesulfonate (414 mg, 0.95 mmol) was dissolved into anhydrous DMF (15 mL), solid NaN3 (186 mg, 2.86 mmol) was added and the reaction mixture was heated to 80° C. overnight. The reaction mixture was cooled to room temperature and diluted with ethyl acetate, the organic phase was washed with water and brine, dried over Na2SO4 and concentrated in vacuo to the crude product (270 mg, 74%), which was used for next step without purification.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washthe organic phase was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo to the crude product (270 mg, 74%), which
  6. customwas used for next step without purification

Sources & evidence

ORD record
ord-efe3c7c5103c4af5bac1c27b632a453e
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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