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Water → 2-(Azidomethyl)-6-(2,2,2-trifluoroethoxy)pyridine

HRID 623431
Notes
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Reaction equation

HRID 623431 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])[N:4]=1.[N-:15]=[N+:16]=[N-:17].[Na+].O>CN(C)C(=O)C>[N:15]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])[N:4]=1)=[N+:16]=[N-:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 622388462-(Chloromethyl)-6-(2,2,2-trifluoroethoxy)pyridine

Product 1

HCID 1317340902-(Azidomethyl)-6-(2,2,2-trifluoroethoxy)pyridineYield 122.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(chloromethyl)-6-(2,2,2-trifluoroethoxy)pyridine (0.35 g, 1.55 mmol, Step-4) and sodium azide (0.20 g, 3.10 mmol) in N,N-dimethylacetamide (8 mL) is stirred 90° C. for 1 hour. The reaction mixture is poured into water (50 mL), and extracted with n-hexane/ethyl acetate (1:10, 50 mL). The organic layer is washed with water (50 mL) and dried over sodium sulfate. The organic fraction is concentrated in vacuo to give 0.44 g (>99% yield) of the title compound as colorless oil. This material is used for the next reaction (Step-6) without further purification.

Workup

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

Sources & evidence

ORD record
ord-eacc9be8f21641c19a5e6601489c67e0
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09302991B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes