Oxalyl chloride → n-((1r)-1-Phenylethyl)(3-bromo-4-methylphenyl)carboxamide

HRID 460159Notes

Reaction equation

HRID 460159 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.[CH3:18][C@@H:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.BrC1C=C(C=CC=1C)C(Cl)=O>C(Cl)Cl.CN(C=O)C>[C:20]1([C@H:19]([NH:26][C:5]([C:4]2[CH:8]=[CH:9][C:10]([CH3:11])=[C:2]([Br:1])[CH:3]=2)=[O:7])[CH3:18])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 821303-Bromo-4-methylbenzoic acidHCID 6431891-Phenethylamine, (+)-HCID 27570573-Bromo-4-methylbenzoyl chloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-4-methylbenzoic acid (5.0 g, 0.023 mol) in CH2CH2 (100 mL) was added oxalyl chloride (8.67 g, 0.069 mol). After 10 minutes, 1.0 mL of DMF was added slowly and the mixture was continued to stir at RT for 2 hours. The volatile was removed in vacuo. The residue was re-dissolved in CH2CH2 (100 mL) and transferred to a 125 mL additional funnel. To a 500 mL Erlenmeyer flask equipped with a stir bar was added 100 m]L 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. customThe volatile was removed in vacuo
  2. dissolutionThe residue was re-dissolved in CH2CH2 (100 mL)
  3. customtransferred to a 125 mL additional funnel
  4. customTo a 500 mL Erlenmeyer flask equipped with a stir bar
  5. additionwas added 100 m]L of sat. aq. NaHCO3 solution
  6. stirringto stir at RT for 16 hours
  7. additionThe organic phase was diluted with 50 mL of CH2CH2
  8. customseparated from aqueous phase
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated in vacuo
  11. washThe residue was washed with 50 mL of Et2O
  12. customdried in an oven at 40 C overnight

Sources & evidence

ORD record
ord-0acc4aa58fe84935bb3fb84914b4cfbe
Source dataset
uspto-grants-2007_03
Patent number
US07196102B2

Reaction notes

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