Sodium Hydroxide → N-benzyl-2,3,4-trifluoro-N-(2-hydroxyethyl)benzamide

HRID 548669Notes

Reaction equation

HRID 548669 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH2:13]([NH:20][CH:21](O)[CH3:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-:24].[Na+]>C(Cl)Cl>[CH2:13]([N:20]([CH2:21][CH2:22][OH:24])[C:4](=[O:5])[C:3]1[CH:7]=[CH:8][C:9]([F:12])=[C:10]([F:11])[C:2]=1[F:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27340222,3,4-Trifluorobenzoyl chlorideHCID 18470673N-benzyl-1-hydroxy-ethylamine

Product 1

HCID 57663176N-benzyl-2,3,4-trifluoro-N-(2-hydroxyethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2,3,4-Trifluorobenzoylchloride (195 mg, 1 mmol) in DCM (1 mL) was added to a stirred solution of N-benzylaminoethanol (166 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 (190 mg). 1H NMR δ (CDCl3): 3.74 (t, 2H), 3.82 (t, 2H), 4.5 (s, 2H), 4.85 (s, 1H), 7.06 (td, 1H), 7.15 (m, 1H), 7.28-7.37 (m, 1H). m/z 310 (M+H)+

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-e0651f92c9204a05a36579039c61cb44
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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