Oxalyl chloride → 2-(4-Bromophenyl)-N-{2-(3-methoxyphenyl)ethyl}-N-phenylacetamide

HRID 1357981Notes

Reaction equation

HRID 1357981 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26](Cl)=[O:27])=[CH:21][CH:20]=1.BrC(C1C=CC=CC=1)C(Cl)=O.C(Cl)(=O)C(Cl)=O>C(OCC)(=O)C.C(Cl)Cl.O>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([N:11]([CH2:10][CH2:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:27])=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 181552Benzeneacetyl chloride, 4-bromo-HCID 598182Bromophenylacetyl chlorideHCID 13467414HCID 13467414, compound

Product 1

HCID 234407982-(4-Bromophenyl)-N-{2-(3-methoxyphenyl)ethyl}-N-phenylacetamideYield 98%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of {2-(3-methoxyphenyl)ethyl}phenylamine (1.06 g, 4.65 mmol) in ethyl acetate (80 mL) under nitrogen was added a solution of 4-bromophenylacetyl chloride (1.06 g, 4.65 mmol) in ethyl acetate (20 mL), the bromophenylacetyl chloride being prepared from the corresponding carboxylic acid (1 g, 4.65 mmol) and oxalyl chloride (0.61 mL, 6.98 mmol) in CH2Cl2 (20 mL). After 1 hour, the reaction was poured into water (50 mL). The organic layer was dried over MgSO4, filtered and concentrated to provide the title compound (1.92 g, 98% yield): EI-MS (m/z) 423.

Workup

  1. dry with materialThe organic layer was dried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-aad31fa182aa4d619773f95b909848a3
Source dataset
uspto-grants-2003_07
Patent number
US06593322B1

Reaction notes

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