Pyridine → 2-Fluoromethyl-2-phthalimido-5-methanesulfonyloxypentanenitrile

HRID 1995567Notes

Reaction equation

HRID 1995567 reaction equation
[F:1][CH2:2][C:3]([N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20])([CH2:6][CH2:7][CH2:8][OH:9])[C:4]#[N:5].N1C=CC=CC=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[F:1][CH2:2][C:3]([N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20])([CH2:6][CH2:7][CH2:8][O:9][S:28]([CH3:27])(=[O:30])=[O:29])[C:4]#[N:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 147716552-Fluoromethyl-2-phthalimido-5-hydroxypentanenitrile

Product 1

HCID 198510892-Fluoromethyl-2-phthalimido-5-methanesulfonyloxypentanenitrileYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-fluoromethyl-2-phthalimido-5-hydroxy-valeronitrile (42.8 g), dry pyridine (170 ml), and dry dichloromethane (350 ml) is stirred and cooled with ice/salt mixture. Freshly distilled methanesulfonylchloride (15.7 g) in dichloromethane (200 ml) is slowly added, and stirring is continued at room temperature overnight. The mixture is then poured onto ice/2 N HCl, and the organic phase is extracted subsequently with 1 N HCl, water, 10% sodium bicarbonate, and water (3×). Drying (MgSO4), treatment with charcoal (room temperature), and evaporation gives the title compound as a brown oil (42 g).

Workup

  1. temperaturecooled with ice/salt mixture
  2. stirringstirring
  3. additionThe mixture is then poured onto ice/2 N HCl
  4. extractionthe organic phase is extracted subsequently with 1 N HCl, water, 10% sodium bicarbonate, and water (3×)
  5. dry with materialDrying (MgSO4), treatment
  6. customwith charcoal (room temperature), and evaporation

Sources & evidence

ORD record
ord-5dc3b55423b84d9c9ddfdfe7f72f78d3
Source dataset
uspto-grants-1983_09
Patent number
US04405530

Reaction notes

Loading…