Pyridine → HCID 14579489, compound

HRID 1995574Notes

Reaction equation

HRID 1995574 reaction equation
[F:1][CH2:2][C:3]([N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])([CH2:6][CH2:7][CH2:8][CH2:9][OH:10])[C:4]#[N:5].N1C=CC=CC=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl>[F:1][CH2:2][C:3]([N:11]1[C:12](=[O:21])[C:13]2=[CH:20][CH:19]=[CH:18][CH:17]=[C:14]2[C:15]1=[O:16])([CH2:6][CH2:7][CH2:8][CH2:9][O:10][S:29]([CH3:28])(=[O:31])=[O:30])[C:4]#[N:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 14579488HCID 14579488, compound

Product 1

HCID 14579489HCID 14579489, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-fluoromethyl-2-phthalimido-6-hydroxy-hexanenitrile (9.0 g, 31 mmol) and pyridine (60 ml) in dry dichloromethane (150 ml) is cooled in an ice bath, and methanesulfonyl chloride (3.6 g, 31 mmol), diluted with a small amount of dichloromethane, is added slowly with efficient stirring. Stirring is continued at room temperature overnight. The reaction mixture is washed with 2 N HCl and dried. Evaporation of solvent gives the title compound as a yellow oil (10.84 g).

Workup

  1. additionis added slowly with efficient stirring
  2. washThe reaction mixture is washed with 2 N HCl
  3. customdried
  4. customEvaporation of solvent

Sources & evidence

ORD record
ord-87f776a7665f4403bbcbdfb7bdce6951
Source dataset
uspto-grants-1983_09
Patent number
US04405530

Reaction notes

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