Water → HCID 63512177, compound

HRID 1629905Notes

Reaction equation

HRID 1629905 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[C:5]#[N:6].[CH3:11][N:12]([CH3:18])[CH:13]1[CH2:17][CH2:16][NH:15][CH2:14]1.[H-].[Na+].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:15]1[CH2:16][CH2:17][CH:13]([N:12]([CH3:18])[CH3:11])[CH2:14]1)[C:5]#[N:6]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1455253-Chloro-4-fluorobenzonitrileHCID 27585193-(Dimethylamino)pyrrolidine

Product 1

HCID 63512177HCID 63512177, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.75 g (4.82 mmol) 3-chloro-4-fluoro-benzonitrile together with 0.65 ml (0.58 g, 5.06 mmol) 3-dimethylamino-pyrrolidine in 12 ml DMF are combined with 231 mg (5.30 mmol) 55% sodium hydride dispersion at ambient temperature with stirring and under an argon atmosphere. After stirring at ambient temperature for 3.5 h the reaction mixture is poured into water and extracted with ethyl acetate after thorough mixing. The combined organic phases are washed with sat. sodium chloride solution, dried over magnesium sulphate and evaporated down completely i. vac.

Workup

  1. stirringAfter stirring at ambient temperature for 3.5 h the reaction mixture
  2. extractionextracted with ethyl acetate after thorough mixing
  3. washThe combined organic phases are washed with sat. sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated down completely i

Sources & evidence

ORD record
ord-8ed309fda0fc4984993e14419fc7cfce
Source dataset
uspto-grants-2014_07
Patent number
US08791103B2

Reaction notes

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