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

HRID 22300
ノート
印刷プレビュー

反応式

HRID 22300 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

HCID 178425847N-[4,4-bis(trifluoromethyl)-2-(4-methylphenyl)-4,5-dihydro-1H-imidazol-5-ylidene]-4-methylbenzamide収率 4.1%

試薬・触媒・溶媒 1

HCID 6212
Chloroform
溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cd7f586fe14b4bd7ad06633c72f17d5a
出典データセット
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05428041

反応ノート

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