2,4-Dibromoaniline → HCID 15485768, compound

HRID 324289Notes

Reaction equation

HRID 324289 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([Br:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[H-].[Na+].Cl[C:13]1[C:14](=[O:25])[N:15]([CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH:16]=[C:17]([Cl:19])[N:18]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:8]=[C:7]([Br:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:13]1[C:14](=[O:25])[N:15]([CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH:16]=[C:17]([Cl:19])[N:18]=1

Participants

5

Reactant 3

HCID 120042,4-DibromoanilineHCID 24758Sodium hydrideHCID 220043393,5-dichloro-1-(1-ethylpropyl)-2(1H)-pyrazinone

Product 1

HCID 15485768HCID 15485768, compoundYield 44.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,4-Dibromoaniline (500 mg), toluene (8 mL), and sodium hydride (60% in oil, 398 mg) were stirred for 10 minutes at room temperature and then 3,5-dichloro-1-(1-ethylpropyl)-2(1H)-pyrazinone (468 mg, Example 1, part B) was added. The reaction was heated at reflux 3 hours, cooled, and quenched with water (50 mL). The mixture was extracted with ethyl acetate (100 mL), which was washed with brine, then dried and concentrated. The crude product was chromatographed on silica gel using ethyl acetate/hexane (1:19) affording 400 mg of material, which was crystallized from ether/hexane to give the title compound (240 mg). Elemental analysis: calcd. for C15H16N3OClBr2: C, 40.07; H, 3.597; N, 9.356; Cl, 7.895; Br, 35.55. Found: C, 40.41; H, 3.49; N, 9.34; Cl, 8.27; Br, 35.71.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux 3 hours
  3. temperaturecooled
  4. customquenched with water (50 mL)
  5. extractionThe mixture was extracted with ethyl acetate (100 mL), which
  6. washwas washed with brine
  7. customdried
  8. concentrationconcentrated
  9. customThe crude product was chromatographed on silica gel

Sources & evidence

ORD record
ord-015eafbcfff3440d9871cc32c6bd1dac
Source dataset
uspto-grants-2001_04
Patent number
US06218391B1

Reaction notes

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