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

HRID 1105616

Reaction equation

HRID 1105616 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 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-fluoromethyl-2-amino-5-methoxy-valeronitrile (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, 1 N HCl, water again, and drying (Na2SO4), the solvent is removed under reduced pressure to give 2.4 g (83%) of crude material. This is purified by chromatography on silica (ethyl acetate/petroleum ether 3:7).

Workup

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

Sources & evidence

ORD record
ord-f424102e49bf4bb398b7c042219a46de
Source dataset
uspto-grants-1982_01
Patent number
US04309442

Linked notes

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