1-(2-Hydroxyethyl)-2-pyrrolidinone → 2-(2-Pyrrolidon-1-yl)ethyl 5-(4-Chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-2,4-dichlorobenzoate

HRID 1870094Notes

Reaction equation

HRID 1870094 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[C:13]([Cl:22])=[CH:14][C:15]([Cl:21])=[C:16]([CH:20]=2)[C:17](Cl)=[O:18])=[N:4][N:5]([CH3:11])[C:6]=1[O:7][CH:8]([F:10])[F:9].[N:23]1([CH2:29][CH2:30][OH:31])[CH2:27][CH2:26][CH2:25][C:24]1=[O:28]>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([C:12]2[C:13]([Cl:22])=[CH:14][C:15]([Cl:21])=[C:16]([CH:20]=2)[C:17]([O:31][CH2:30][CH2:29][N:23]2[CH2:27][CH2:26][CH2:25][C:24]2=[O:28])=[O:18])=[N:4][N:5]([CH3:11])[C:6]=1[O:7][CH:8]([F:10])[F:9]

Participants

4

Reactant 2

HCID 769801-(2-Hydroxyethyl)-2-pyrrolidinoneHCID 153463895-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-2,4-dichlorobenzoyl chloride

Product 1

HCID 186951752-(2-Pyrrolidon-1-yl)ethyl 5-(4-Chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-2,4-dichlorobenzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1 g (2.6 mmol) of 5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-2,4-dichlorobenzoyl chloride and 0.5 g (3.8 mmol) of 2-(2-pyrrolidon-1-yl)ethanol in 20 ml of pyridine was stirred for approximately 15 hours, whereupon the reaction mixture was concentrated. The residue was treated with 10 ml of water and 20 ml of ethyl acetate. The organic phase was then separated off, dried over magnesium sulfate and concentrated. The crude product was purified by column chromatography on silica gel (eluent: initially hexane/ethyl acetate=1:1, then ethyl acetate). Yield: 0.8 g.

Workup

  1. concentrationwas concentrated
  2. additionThe residue was treated with 10 ml of water and 20 ml of ethyl acetate
  3. customThe organic phase was then separated off
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography on silica gel (eluent

Sources & evidence

ORD record
ord-42f718896fd74ac390c311ec4eba0731
Source dataset
uspto-grants-2000_08
Patent number
US06096689

Reaction notes

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