Trimethyl orthobeznoate → 1-Benzyl-5-bromo-2-phenyl-1H-benzo[d]imidazole

HRID 1993207노트

반응식

HRID 1993207 반응식
[CH2:1]([NH:8][C:9]1[C:10]([NH2:16])=[CH:11][C:12]([Br:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:19](OC)(OC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[CH2:1]([N:8]1[C:9]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=2[N:16]=[C:19]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 69720Trimethyl orthobeznoateHCID 289029062-Benzylamino-5-bromoaniline

생성물 1

HCID 591330541-Benzyl-5-bromo-2-phenyl-1H-benzo[d]imidazole

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

p-TsOH-H2O (311.7 mg, 1.606 mmol) was added to a DCM (50 ml) solution of N1-benzyl-4-bromobenzene-1,2-diamine (4451 mg, 16.06 mmol) and trimethyl orthobenzoate (3096 μl, 17.66 mmol) and the resulting mixture was stirred at rt under an atmosphere of Nitrogen for 40 h. The reaction mixture was then concentrated in vacuo to give a yellow solid which was triturated with 40% MeOH/water (375 mL), filtered, washed with saturated NaHCO3 (20 ml)+H2O (80 ml) twice and 40% MeOH/H2O (2×50 ml), and dried to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm =5.44 (s, 2 H), 7.05-7.08 (m, 3 H), 7.30-7.36 (m, 4 H), 7.44-7.50 (m, 3 H), 7.66-7.68 (m, 2 H) and 7.99 (dd, 1 H, J=0.4 & 1.6 Hz). MS(ES+): m/z 363.20 and 365.26[MH+].

후처리

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customto give a yellow solid which
  3. customwas triturated with 40% MeOH/water (375 mL)
  4. filtrationfiltered
  5. washwashed with saturated NaHCO3 (20 ml)+H2O (80 ml) twice
  6. dry with material40% MeOH/H2O (2×50 ml), and dried

출처 및 근거

ORD 기록
ord-e87e036cd80648c68185dd1549ac1216
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07651687B2

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