m-Chloroperbenzoic acid → HCID 178426890, compound

HRID 22306Notes

Reaction equation

HRID 22306 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]([C:25]([F:28])([F:27])[F:26])([C:5]1[N:6](C)C(C2C=CC(C)=CC=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:9]=1)[NH2:4].Cl[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38](OO)=O)[CH:33]=1.[C:42](=[O:45])(O)[O-:43].[Na+]>C(Cl)(Cl)Cl>[CH3:38][C:34]1[CH:35]=[CH:36][C:37]([O:43][C:42](=[O:45])[N:6]=[C:5]2[NH:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=3)=[N:4][C:3]2([C:25]([F:28])([F:26])[F:27])[C:2]([F:1])([F:30])[F:29])=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 19927760alpha,alpha-bis(trifluoromethyl)-4,5-bis(4-methylphenyl)-1-methyl-1H-imidazol-2-methanamine

Product 1

HCID 178426890HCID 178426890, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of α,α-bis(trifluoromethyl)-4,5-bis(4-methylphenyl)-1-methyl-1H-imidazol-2-methanamine (1.0 g, 2.3 mmole) in chloroform (10 mL) was added portionwise, m-chloroperbenzoic acid (1.20 g, 7 mmole). The reaction mixture was refluxed under nitrogen for two hours. The solution was cooled to room temperature and poured into saturated sodium bicarbonate (100 mL). The organic layer was washed successively with saturated sodium bicarbonate solution, 10% sodium sulfite solution, water, and saturated sodium chloride solution, dried over magnesium sulfate and evaporated under vacuum. The residue was triturated with petroleum ether to give the title compound (0.15 g, 14%) as a solid: mp 161°-163°; MS m/e 458 (M+ +H); 1H NMR (CDCl3 /TMS) δ 2.43 (s,6H,CH3), 3.06(s,3H,NCH3), 7.23-7.40(m,4H,Harom), 7.50-7.63(m,2H,Harom), 7.87-7.93(m,2H,Harom).

Workup

  1. temperatureThe reaction mixture was refluxed under nitrogen for two hours
  2. washThe organic layer was washed successively with saturated sodium bicarbonate solution, 10% sodium sulfite solution, water, and saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under vacuum
  5. customThe residue was triturated with petroleum ether

Sources & evidence

ORD record
ord-1af8f49437224334b18f06e47cd8e62b
Source dataset
uspto-grants-1995_06
Patent number
US05428041

Reaction notes

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