Water → HCID 131734088, compound

HRID 715350Notes

Reaction equation

HRID 715350 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH3:15])[C:6]([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[N:7][CH:8]=1.[N-:16]=[N+:17]=[N-:18].[Na+].O>CC(N(C)C)=O>[N:16]([CH2:2][C:3]1[CH:4]=[C:5]([CH3:15])[C:6]([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[N:7][CH:8]=1)=[N+:17]=[N-:18]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 67508778HCID 67508778, compound

Product 1

HCID 131734088HCID 131734088, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-(chloromethyl)-3-methyl-2-(2,2,2-trifluoroethoxy)pyridine (0.75 g, 3.15 mmol, Step-3) and sodium azide (0.41 g, 6.29 mmol) in DMA (8 mL) is stirred at 90° C. for 2 hours. The reaction mixture is poured into water (50 mL), and extracted with n-hexane/EtOAc (1:10, 50 mL). The organic layer is washed with water (50 mL) and dried over sodium sulfate. After filtration, the organic fraction is concentrated in vacuo to give 0.77 g (>99% yield) of the title compound as colorless oil. This material is used for the next reaction (Step-5) without further purification.

Workup

  1. extractionextracted with n-hexane/EtOAc (1:10, 50 mL)
  2. washThe organic layer is washed with water (50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe organic fraction is concentrated in vacuo

Sources & evidence

ORD record
ord-22ad446b196b4be2aac6ef174c4823a7
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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