Ethanolamine → N-(2-hydroxyethyl)-2-iodobenzamide

HRID 1012346Notes

Reaction equation

HRID 1012346 reaction equation
C(=O)([O-])O.[Na+].[NH2:6][CH2:7][CH2:8][OH:9].[I:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14]>C(OCC)(=O)C.O>[OH:9][CH2:8][CH2:7][NH:6][C:13](=[O:14])[C:12]1[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=1[I:10]

Participants

6

Reactant 3

HCID 700EthanolamineHCID 691122-Iodobenzoyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 2186617N-(2-hydroxyethyl)-2-iodobenzamideYield 87.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of sodium hydrogen carbonate (3.30 g, 39.7 mmol) and 2-aminoethanol (1.80 ml, 29.8 mmol) in ethyl acetate (25 ml) and water (15 ml) was added dropwise the solution of 2-iodobenzoyl chloride in ethyl acetate prepared above under ice-cooling, and the mixture was stirred at room temperature for 12 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to give N-(2-hydroxyethyl)-2-iodobenzamide (5.12 g, yield 87.6%).

Workup

  1. customprepared above under ice-
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5e4c8df6dca14f53aa806e5babad5885
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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