N-bromobutanimide → HCID 14696385, compound

HRID 1089578Notes

Reaction equation

HRID 1089578 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[Br:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:20])[CH:18]=2)[CH:13]=[CH:12][CH:11]=1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[CH:18]=[C:17]([CH2:20][Br:8])[CH:16]=[CH:15]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 3473541-bromo-7-methylnaphthalene

Product 1

HCID 14696385HCID 14696385, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent2×

Procedure

To boiling CCl4 (250 mL) was added NBS (20.4 g, 0.114 mol) and AIBN (1.4 g, 0.009 mol). After 1 minute, a solution of 1-bromo-7-methylnaphthalene (24.1 g, 0.109 mol) in CCl4 (15 mL) was added all at once. Within 1 minute, the reaction became quite exothermic and the heating mantle was removed for several minutes. Heating was resumed for 30 minutes. The mixture was cooled, filtered, and the filtrate was concentrated to give an off-white solid (32.7 g). The product ws combined with similarly prepared material (32.6 g) and recrystallized from ethyl acetate/hexane to give the product (29.6 g, 45%).

Workup

  1. waitWithin 1 minute
  2. customthe heating mantle was removed for several minutes
  3. temperatureHeating
  4. waitwas resumed for 30 minutes
  5. temperatureThe mixture was cooled
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-43a07bcd3ac343c8bb5610bd44df4571
Source dataset
uspto-grants-1990_10
Patent number
US04966975

Reaction notes

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