2-(Ethylamino)ethanol → 3-Chloro-N-ethyl-2,4-difluoro-N-(2-hydroxyethyl)benzamide

HRID 548671

Reaction equation

HRID 548671 reaction equation
[Cl:1][C:2]1[C:3]([F:12])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5](Cl)=[O:6].[CH2:13]([NH:15][CH2:16][CH2:17][OH:18])[CH3:14]>C(Cl)Cl.[OH-].[Na+]>[Cl:1][C:2]1[C:3]([F:12])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([N:15]([CH2:13][CH3:14])[CH2:16][CH2:17][OH:18])=[O:6]

Participants

5

Reactant 2

HCID 80722-(Ethylamino)ethanolHCID 27735383-Chloro-2,4-difluorobenzoyl chloride

Product 1

HCID 576632233-Chloro-N-ethyl-2,4-difluoro-N-(2-hydroxyethyl)benzamideYield 83.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

3-Chloro-2,4-difluorobenzoylchloride (211 mg, 1 mmol) in DCM (1 mL) was added to a stirred solution of 2-(ethylamino)ethanol (98 mg, 1.1 mmol) in a mixture of DCM (1 mL) and 10% sodium hydroxide solution (1 mL) at 0° C. After the addition of the acid chloride was complete, the mixture was warmed to RT and stirred for approximately 4 hours. The two layers were separated and the aqueous layer was extracted with DCM (3×30 mL). The organic layers were combined, dried (MgSO4), filtered and evaporated to give a colourless oil (220 mg). The material was used without further purification or analysis.

Workup

  1. customThe two layers were separated
  2. extractionthe aqueous layer was extracted with DCM (3×30 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-27bd019121244aa983971f73c4b2dc9a
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Linked notes

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