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2,6-Dichloro-4-(trifluoromethyl)phenylacetic acid → 2-[2,6-Dichloro-4-(trifluoromethyl)benzyl]-1-methyl-1H-benzimidazol-7-amine

HRID 1665224
ノート
印刷プレビュー

反応式

HRID 1665224 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[CH2:13][C:14](O)=O.[CH3:17][NH:18][C:19]1[C:24]([NH2:25])=[CH:23][CH:22]=[CH:21][C:20]=1[NH2:26]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[CH2:13][C:14]1[N:18]([CH3:17])[C:19]2[C:24]([NH2:25])=[CH:23][CH:22]=[CH:21][C:20]=2[N:26]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 27368722,6-Dichloro-4-(trifluoromethyl)phenylacetic acidHCID 12296380N2-Methylbenzene-1,2,3-triamine

生成物 1

HCID 592020902-[2,6-Dichloro-4-(trifluoromethyl)benzyl]-1-methyl-1H-benzimidazol-7-amine収率 45.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
50 °C

実験手順

To a solution of [2,6-dichloro-4-(trifluoromethyl)phenyl]acetic acid (273 mg, 1.00 mmol) in toluene (2.0 mL) was added N,N′-carbonyldiimidazole (162 mg, 1.00 mmol) at room temperature. After the reaction mixture was stirred at 50° C. for 15 min, N2-methylbenzene-1,2,3-triamine (137 mg, 1.00 mmol) in toluene (2 mL) was added to the mixture, and the mixture was refluxed for further 60 hr. After the reaction mixture was cooled, the solvent was evaporated in vacuo, and the residue was purified by silica gel column chromatography eluting with 40-60% ethyl acetate/n-hexane gradient mixture to give the title compound (170 mg, 0.455 mmol, 45%) as a colorless solid. The resulting solid was recrystallized from n-hexane/ethyl acetate to give the title compound (137 mg, 0.38 mmol).

後処理

  1. temperaturethe mixture was refluxed for further 60 hr
  2. temperatureAfter the reaction mixture was cooled
  3. customthe solvent was evaporated in vacuo
  4. customthe residue was purified by silica gel column chromatography
  5. washeluting with 40-60% ethyl acetate/n-hexane gradient mixture

出典と根拠

ORDレコード
ord-2bee90d555524516ab1e2fed9718c21c
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08039500B2

反応ノート

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