Pyridine → HCID 14579489, compound

HRID 1607764Notes

Reaction equation

HRID 1607764 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-hydroxyhexanenitrile (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 2N HCl and dried. Evaporation of solvent gives 2-fluoromethyl-2-phthalimido-6-methanesulfonyloxyhexanenitrile as a yellow oil (10.84 g).

Workup

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

Sources & evidence

ORD record
ord-0643068e768f46a8afbbc4bb01bf38b2
Source dataset
uspto-grants-1989_09
Patent number
US04866206

Reaction notes

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