Trifluoroacetic acid → 4-Methylbenzimidazole

HRID 8959

반응식

HRID 8959 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-bf56584023f540c7948984614ab8fea3
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091217B2

연결된 노트

불러오는 중…