Benzoyl Peroxide → HCID 58976527, compound

HRID 601050Notes

Reaction equation

HRID 601050 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[N:5]=[C:4]([NH:15][C:16]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]([CH3:24])=[C:18]([O:25][CH3:26])[CH:17]=2)[N:3]=1.C1C(=O)N([Br:34])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C1C=CC=CC=1>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]([C:11]#[N:12])=[CH:13][CH:14]=2)[N:5]=[C:4]([NH:15][C:16]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]([CH3:24])=[C:18]([O:25][CH3:26])[C:17]=2[Br:34])[N:3]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 58976466HCID 58976466, compound

Product 1

HCID 58976527HCID 58976527, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

To a suspension of 4-[5-Amino-3-(3,5-dimethoxy-4-methyl-phenylamino)-[1,2,4]triazol-1-yl]-benzonitrile (155 mg, 0.44 mmol) in CCl4 (10 mL) and benzene (10 mL) was added N-bromosuccimide (100 mg, 0.56 mmol) and benzoyl peroxide (10 mg). The reaction mixture was refluxed for 16 h. Concentration. The residue was purified by HPLC to give the title compound (80 mg). FIA-MS: m/e=429.1 and 431.1 (M+H), 427.1 and 429.1 (M−H). Rt=3.89 min (Method A). 1H-NMR (500 MHz, DMSO(d6)): 7.95 (d, 2H), 7.82 (s, 1H), 7.80 (d, 2H), 7.37 (s, 1H), 6.88 (br. s, 2H), 3.80 (s, 3H), 3.69 (s, 3H), 2.08 (s, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. concentrationConcentration
  3. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-4cce58b2f1f7414f84497dcb307483bf
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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