Phthaloyl chloride → 2-Fluoromethyl-2-phthalimido-5-methoxypentanenitrile

HRID 1252564Notes

Reaction equation

HRID 1252564 reaction equation
[F:1][CH2:2][C:3]([NH2:11])([CH2:6][CH2:7][CH2:8][O:9][CH3:10])[C:4]#[N:5].C(N(CC)CC)C.[C:19](Cl)(=[O:29])[C:20]1[C:21](=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:22](Cl)=[O:23]>C(Cl)Cl>[F:1][CH2:2][C:3]([N:11]1[C:22](=[O:23])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]2[C:19]1=[O:29])([CH2:6][CH2:7][CH2:8][O:9][CH3:10])[C:4]#[N:5]

Participants

5

Reactant 3

HCID 6955Phthaloyl chlorideHCID 8471TriethylamineHCID 199663342-Amino-2-(fluoromethyl)-5-methoxypentanenitrile

Product 1

HCID 199663292-Fluoromethyl-2-phthalimido-5-methoxypentanenitrileYield 82.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-fluoromethyl-2-amino-5-methoxypentanenitrile (1.62 g, 10 mmol) and triethylamine (2.02 g, 20 mmol) in methylene chloride (30 ml), cooled to -20° C., is added phthaloyldichloride (2.03 g, 10 mmol) in methylene chloride (10 ml). The mixture is allowed to warm up to room temperature overnight. After washing with water, 1N HCl, water again, and drying (Na2SO4), the solvent is removed under reduced pressure to give 2.4 g of crude material. This is purified by chromatography on silica (ethyl acetate/petroleum ether 3:7).

Workup

  1. washAfter washing with water, 1N HCl, water again
  2. dry with materialdrying (Na2SO4)
  3. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-f102d11c384048eeaac8cb3e971c5ea6
Source dataset
uspto-grants-1988_05
Patent number
US04743691

Reaction notes

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