Azobisisobutyronitrile → 4'-(Bromomethyl)-[1,1'-biphenyl]-2-carboxamide

HRID 1080825Notes

Reaction equation

HRID 1080825 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH2:16])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C1C=CC=CC=1>[Br:17][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH2:16])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 101713452-(p-Tolyl)benzamide

Product 1

HCID 152190064'-(Bromomethyl)-[1,1'-biphenyl]-2-carboxamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4'-methylbiphenyl-2-carboxamide (2.1 g), N-bromo-succinimide (2.5 g) and azobisisobutyronitrate (AIBN;82 mg) in benzene (20 ml) was stirred for 20 hours at 60° to 70° C. Resulting crystalline precipitates were collected by filtration, washed with isopropylether and suspended in water. The suspension was stirred for 30 minutes, and insoluble materials were collected by filtration and dried to give crude crystals. Recrystallization from ethyl acetate--methanol afforded colorless needles (1.6 g, 55%), m.p. 220°-221° C.(decomp.).

Workup

  1. customResulting crystalline precipitates
  2. filtrationwere collected by filtration
  3. washwashed with isopropylether
  4. stirringThe suspension was stirred for 30 minutes
  5. filtrationinsoluble materials were collected by filtration
  6. customdried
  7. customto give crude crystals
  8. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-bc895f67515b40b191349f031f0bfc10
Source dataset
uspto-grants-1996_12
Patent number
US05583141

Reaction notes

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