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Ethanolamine → 2,4-difluoro-N-(2-hydroxyethyl)benzamide

HRID 51001
Notes
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Reaction equation

HRID 51001 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[F:5][C:6]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:7]=1[C:8](Cl)=[O:9]>C1COCC1.C(OCC)(=O)C>[F:5][C:6]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:7]=1[C:8]([NH:4][CH2:3][CH2:1][OH:2])=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 700EthanolamineHCID 5880812,4-Difluorobenzoyl chloride

Product 1

HCID 176835502,4-difluoro-N-(2-hydroxyethyl)benzamideYield 87%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Procedure

To a solution of ethanolamine (1.10 g, 15.8 mmol) in THF at 0° C. under N2 was added 2,4-difluorobenzoyl chloride (500 mg, 2.83 mmol). The reaction mixture was stirred at 0° C. for 4 h, then diluted with ethyl acetate (100 mL) and washed with 1 N HCl (50 mL), saturated NaHCO3 (50 mL), and saturated NaCl (50 mL). The organic solution was dried over MgSO4 and concentrated in vacuo to yield 2,4-difluoro-N-(2-hydroxyethyl)benzamide as a white solid (495 mg, 87%).

Workup

  1. washwashed with 1 N HCl (50 mL), saturated NaHCO3 (50 mL), and saturated NaCl (50 mL)
  2. dry with materialThe organic solution was dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-084e64c90f2c4f3cbc32025195d73cff
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06713471B1

Reaction notes

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