Sodium Chloride → HCID 59570322, compound

HRID 1880735Notes

Reaction equation

HRID 1880735 reaction equation
[H-].[Na+].[F:3][C:4]([F:11])([C:7]([F:10])([F:9])[F:8])[CH2:5][OH:6].Cl[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]#[N:20])[CH:14]=1.[Cl-].[Na+]>CN(C)C=O>[F:3][C:4]([F:11])([C:7]([F:10])([F:9])[F:8])[CH2:5][O:6][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]#[N:20])[CH:14]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 98722,2,3,3,3-PentafluoropropanolHCID 24758Sodium hydrideHCID 6933424-Chloro-2-pyridinecarbonitrile

Product 1

HCID 59570322HCID 59570322, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 6 ml of N,N-dimethylformamide was suspended 0.16 g of sodium hydride (60% oily), and 0.52 g of 2,2,3,3,3-pentafluoro-1-propanol was added at 10° C. After stirring for 25 minutes, 0.4 g of 4-chloropyridine-2-carbonitrile was added, the mixture was stirred for 3 hours, and the reaction solution was poured into an aqueous saturated sodium chloride solution, followed by extraction with tert-butyl=methyl=ether three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.55 g of 4-(2,2,3,3,3-pentafluoropropoxy)pyridine-2-carbonitrile.

Workup

  1. additionwas added at 10° C
  2. stirringthe mixture was stirred for 3 hours
  3. extractionfollowed by extraction with tert-butyl=methyl=ether three times
  4. washwashed with an aqueous saturated sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-21f402f42d934474aa165836a1e45683
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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