Sodium Bicarbonate → n-((1r)-1-Phenylethyl)(3-bromo-4-methylphenyl)carboxamide

HRID 2113136Notes

Reaction equation

HRID 2113136 reaction equation
C([O-])(O)=O.[Na+].[CH3:6][C@@H:7]([NH2:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:19](Cl)=[O:20]>C(Cl)Cl>[C:8]1([C@H:7]([NH:14][C:19]([C:18]2[CH:22]=[CH:23][C:24]([CH3:25])=[C:16]([Br:15])[CH:17]=2)=[O:20])[CH3:6])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 6431891-Phenethylamine, (+)-HCID 27570573-Bromo-4-methylbenzoyl chloride

Product 1

HCID 681076n-((1r)-1-Phenylethyl)(3-bromo-4-methylphenyl)carboxamideYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 500 mL Erlenmeyer flask equipped with a stir bar was added 100 mL of sat. aq. NaHCO3 solution followed by 2.79 g of (R)-α-methylbenzylamine (0.023 mol) in 100 mL of CH2CH2. 3-Bromo-4-methylbenzoyl chloride in CH2Cl2 (from above) was added dropwise to the Erlenmeyer flask and the reaction mixture was continued to stir at RT for 16 hours. The organic phase was diluted with 50 mL of CH2CH2, separated from aqueous phase, dried over Na2SO4 and concentrated in vacuo. The residue was washed with 50 mL of Et2O and dried in an oven at 40 C overnight to afford light yellow solid (7.0 g, 0.022 mol, 96%).

Workup

  1. customTo a 500 mL Erlenmeyer flask equipped with a stir bar
  2. additionThe organic phase was diluted with 50 mL of CH2CH2
  3. customseparated from aqueous phase
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with 50 mL of Et2O
  7. customdried in an oven at 40 C overnight

Sources & evidence

ORD record
ord-8c020ec44e184898af17339d51acc71b
Source dataset
uspto-grants-2009_04
Patent number
US07524873B2

Reaction notes

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