N-bromobutanimide → HCID 68086663, compound

HRID 1405064Notes

Reaction equation

HRID 1405064 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12](=[O:14])[CH3:13])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C1C(=O)N([Br:22])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:22][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([NH:11][C:12](=[O:14])[CH3:13])=[CH:6][C:7]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 702039N-(3,5-dimethoxyphenyl)acetamide

Product 1

HCID 68086663HCID 68086663, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-(3,5-Dimethoxyphenyl)acetamide (500 mg, 2.56 mmol) was suspended in CCl4 (3 mL) followed by the addition of NBS (456 mg, 2.56 mmol) at room temperature. The reaction mixture was stirred at room temperature for 0.5 hour, heated at 80° C. for 2 hours and then concentrated under reduced pressure. The crude material was purified by silica gel chromatography (80 g ISCO column, eluting with 0% to 20% EtOAc in CH2Cl2) to provide Intermediate 9A (178 mg, 0.649 mmol, 25.4% yield) as a white solid. MS (ES): m/z=276.0 [M+H]+. 1H NMR (400 MHz, MeOD) δ ppm 2.14 (s, 3 H) 3.85 (s, 6 H) 7.01 (s, 2 H).

Workup

  1. temperatureheated at 80° C. for 2 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe crude material was purified by silica gel chromatography (80 g ISCO column, eluting with 0% to 20% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-4b82cc5e329e475da0a669922ce689ad
Source dataset
uspto-grants-2014_12
Patent number
US08916553B2

Reaction notes

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