Trifluoroacetic acid → 4-Methylbenzimidazole

HRID 1157903

반응식

HRID 1157903 반응식
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[CH3:10]OC(OC)OC.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:9][C:3]1[C:2]2[N:1]=[CH:10][NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 9005Trimethyl orthoformateHCID 175932,3-Diaminotoluene

생성물 1

HCID 15193414-Methylbenzimidazole

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of 2,3-diaminotoluene (1.00 g, 8.2 mmol) in CH2Cl2 (82 mL) was added trimethylorthoformate (4.5 mL, 41 mmol) and trifluoroacetic acid (0.32 mL, 4.1 mmol) and the mixture stirred at room temperature for 24 h after which the reaction mixture was diluted with CH2Cl2 (200 mL), and washed consecutively with saturated aqueous NaHCO3 (40 mL) and H2O (40 mL). The aqueous layers were reextracted with CH2Cl2 (2×100 mL). The combined organic extracts were dried over MgSO4 and concentrated to a rusty brown solid (1.07 g, 97%). 1H NMR (300 MHz, CDCl3) δ 8.08 (s, 1H), 7.49 (d, 1H, J=8.1 Hz), 7.23-7.18 (m, 1H), 7.10 (d, 1H, J=7.5. Hz), 2.64 (s, 3H).

후처리

  1. washwashed consecutively with saturated aqueous NaHCO3 (40 mL) and H2O (40 mL)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. concentrationconcentrated to a rusty brown solid (1.07 g, 97%)

출처 및 근거

ORD 기록
ord-e0ceb6c6c9294af3b9f2df97c423d212
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807694B2

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