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

HRID 1870927Notes

Reaction equation

HRID 1870927 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

Conditions

Temperature
65 °C

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-methanol afforded colorless needles (1.6 g, 55%), m.p. 220-221° C.(decomp.)

Sources & evidence

ORD record
ord-d101f7e84ad64eeca95fe1b261990935
Source dataset
uspto-grants-2000_08
Patent number
US06100252

Reaction notes

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