(3,5-Dibromo-4-methoxyphenyl)acetylchloride → 2-(3,5-dibromo-4-methoxy-phenyl)-N-[2-(3-nitro-phenyl)-ethyl]-acetamide

HRID 1358473Notes

Reaction equation

HRID 1358473 reaction equation
C(O)(=O)C(O)=O.[N+:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[CH2:13][CH2:14][NH2:15])([O-:9])=[O:8].[Br:19][C:20]1[CH:21]=[C:22]([CH2:29][C:30](Cl)=[O:31])[CH:23]=[C:24]([Br:28])[C:25]=1[O:26][CH3:27]>C(Cl)Cl.[OH-].[Na+]>[Br:19][C:20]1[CH:21]=[C:22]([CH2:29][C:30]([NH:15][CH2:14][CH2:13][C:12]2[CH:16]=[CH:17][CH:18]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=2)=[O:31])[CH:23]=[C:24]([Br:28])[C:25]=1[O:26][CH3:27]

Participants

5

Reactant 2

HCID 18184515(3,5-Dibromo-4-methoxyphenyl)acetylchlorideHCID 181845273-Nitro-phenethylamine oxalate

Product 1

HCID 181845412-(3,5-dibromo-4-methoxy-phenyl)-N-[2-(3-nitro-phenyl)-ethyl]-acetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To a suspension of 3-nitro-phenethylamine oxalate (1.792 g, 0.007 mol) in methylene chloride (45 mL), 1 N NaOH (45 mL) was added. It was stirred at room temperature to get a clear solution. A solution of 3,5-dibromo-4-methoxyphenyl acetyl chloride (0.0072 mol) in methylene chloride was added. Stirring was continued overnight and the completion of the reaction was monitored by thin layer chromatography. The reaction mixture was washed with 1N HCl and 1N NaOH, extracted with methylene chloride. The combined extracts were dried over anhydrous sodium sulfate and concentrated. The solid obtained was crystallized from ethyl acetate-hexanes mixture. Yield 2.159 g, 65%.

Workup

  1. additionwas added
  2. customto get a clear solution
  3. stirringStirring
  4. washThe reaction mixture was washed with 1N HCl and 1N NaOH
  5. extractionextracted with methylene chloride
  6. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe solid obtained
  9. customwas crystallized from ethyl acetate-hexanes mixture

Sources & evidence

ORD record
ord-0f62632f3260459692aad07ca5f7b1d9
Source dataset
uspto-grants-2003_07
Patent number
US06596734B1

Reaction notes

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