2-(Methylamino)ethanol → 3-chloro-2,4-difluoro-N-(2-hydroxyethyl)-N-methylbenzamide

HRID 600558Notes

Reaction equation

HRID 600558 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].[CH3:13][NH:14][CH2:15][CH2:16][OH:17]>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:14]([CH2:15][CH2:16][OH:17])[CH3:13])=[O:6]

Participants

5

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 27735383-Chloro-2,4-difluorobenzoyl chloride

Product 1

HCID 576632133-chloro-2,4-difluoro-N-(2-hydroxyethyl)-N-methylbenzamideYield 61%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

3-Chloro-2,4-difluorobenzoylchloride (CAS no. 157373-00-7) (211 mg, 1 mmol) in DCM (1 mL) was added to a stirred solution of 2-(methylamino)ethanol (83 mg, 1.1 mmol) in a mixture of DCM (1 mL) and 10% sodium hydroxide solution (1 mL) at 0° C. The mixture was warmed to room temperature 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 afford the product (180 mg, 61%). 1H NMR δ (400 MHz, CDCl3): 3.01 (s, 3H), 3.37 (t, 1H), 3.74 (t, 2H), 3.92 (t, 2H), 7.06 (td, 1H), 7.28-7.37 (m, 1H).

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-a98733b8ffdf4d08ba239b9b286180a9
Source dataset
uspto-grants-2011_03
Patent number
US07902200B2

Reaction notes

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