Acetic Anhydride → N-((1S)-1-(4-Bromophenyl)ethyl)acetamide

HRID 1470714Notes

Reaction equation

HRID 1470714 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([NH2:17])[CH3:16])=[CH:11][CH:10]=1.C([O-])(O)=O.[Na+]>ClCCl>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([NH:17][C:5](=[O:7])[CH3:6])[CH3:16])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamine

Product 1

HCID 793484N-((1S)-1-(4-Bromophenyl)ethyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

23.6 mL (250 mmol) acetic anhydride are added to 50.0 g (250 mmol) (S)-1-(4-bromophenyl)-ethylamine in 200 mL dichloromethane while keeping the reaction temperature below 30° C. Stirring is continued for 12 h at rt. After that time, saturated NaHCO3-solution is added. The organic layer is separated, washed with water, dried over magnesium sulphate and the solvent is removed by evaporation.

Workup

  1. customthe reaction temperature below 30° C
  2. customThe organic layer is separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent is removed by evaporation

Sources & evidence

ORD record
ord-b6fee8ddef8e4710a886cd853dea995e
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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