2-(Methylamino)ethanol → 2,4,5-trifluoro-N-(2-hydroxyethyl)-N-methylbenzamide

HRID 548708Notes

Reaction equation

HRID 548708 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:13][NH:14][CH2:15][CH2:16][OH:17]>C(Cl)Cl.[OH-].[Na+]>[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([N:14]([CH2:15][CH2:16][OH:17])[CH3:13])=[O:5]

Participants

5

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 1451642,4,5-Trifluorobenzoyl chloride

Product 1

HCID 576631992,4,5-trifluoro-N-(2-hydroxyethyl)-N-methylbenzamideYield 105.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

2,4,5-Trifluorobenzoyl chloride (540 mg, 2.78 mmol) was added to a stirred solution of 2-methylaminoethanol (0.185 mL, 3.06 mmol) in DCM (5 mL) and 10% aqueous sodium hydroxide solution (5 mL) at 0° C. After addition was complete the icebath was removed and the reaction was allowed to warm up to RT and stirred for 3 hours. The phases were then separated and the aqueous phase extracted with DCM (3×30 mL). The combined organic layers were dried (MgSO4), filtered and evaporated to give the desired compound as a colourless oil (686 mg). This material was used without further purification.

Workup

  1. additionAfter addition
  2. customwas removed
  3. customThe phases were then separated
  4. extractionthe aqueous phase extracted with DCM (3×30 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-12045789a31b42b6861539732f48df04
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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