m-Chloroperbenzoic acid → N-[4,4-bis(trifluoromethyl)-2-(4-methylphenyl)-4,5-dihydro-1H-imidazol-5-ylidene]-4-methylbenzamide

HRID 22300Notes

Reaction equation

HRID 22300 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:7]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:9]=1)[NH2:4].ClC1C=CC=C(C(OO)=[O:39])C=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[F:28][C:25]([F:26])([F:27])[C:3]1([C:2]([F:29])([F:30])[F:1])[C:5](=[N:9][C:8](=[O:39])[C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[NH:6][C:7]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[N:4]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 178425847N-[4,4-bis(trifluoromethyl)-2-(4-methylphenyl)-4,5-dihydro-1H-imidazol-5-ylidene]-4-methylbenzamideYield 4.1%

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 (0.40 g, 2.3 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 (75% benzamide and 25% ester analyzed by HPLC with a (DL)-phenylglycine column eluted with 10% isopropanol-hexane) was purified by HPLC on a silica sorbax column which was eluted with dichloromethane to give the title compound (40 mg, 4%) as a semisolid: MS m/e 442 (M+ +H); 1H NMR (CDCl3 /TMS) δ 3.00(s,6H,CH3), 3.13(s,3H,NCH3), 7.27-7.37(m,4H,Harom), 7.57(d,J= 7 Hz,2H,Harom), 7.90(d,J=7 Hz,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
  3. dry with material10% sodium sulfite solution, water, and saturated sodium chloride solution, dried over magnesium sulfate
  4. customevaporated under vacuum
  5. washeluted with 10% isopropanol-hexane)
  6. customwas purified by HPLC on a silica sorbax column which
  7. washwas eluted with dichloromethane

Sources & evidence

ORD record
ord-cd7f586fe14b4bd7ad06633c72f17d5a
Source dataset
uspto-grants-1995_06
Patent number
US05428041

Reaction notes

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