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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
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HRID 1665224 반응식
[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
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반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

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온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2bee90d555524516ab1e2fed9718c21c
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08039500B2

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