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p-Toluenesulfonic acid monohydrate → 6-bromo-1-(4-methoxybenzyl)-1H-benzo[d]imidazole

HRID 1399823
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HRID 1399823 반응식
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:5]([NH2:18])=[CH:4][CH:3]=1.[CH3:19]C1C=CC(S(O)(=O)=O)=CC=1.O>C(OC)(OC)OC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:18]=[CH:19][N:8]([CH2:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=3)[C:6]=2[CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 653433435-bromo-N-(4-methoxybenzyl)benzene-1,2-diamine

생성물 1

HCID 867292426-bromo-1-(4-methoxybenzyl)-1H-benzo[d]imidazole수율 886.7%

시약·촉매·용매 1

HCID 9005Trimethyl orthoformate용매

반응 조건

온도
100 °C

실험 절차

To a solution of 5-bromo-N-(4-methoxybenzyl)benzene-1,2-diamine (550 mg, crude) in HC(OMe)3 (20 mL) was added TsOH.H2O (30 mg, 0.16 mmol). The mixture was stirred at 100° C. for 4 h. The reaction solution was then concentrated and the residue was washed with water and extracted with EtOAc. The organic layer was concentrated to give the desired product (450 mg, 79% yield) and the crude product used in next step without further purification. LCMS (m/z): 318.1 [M+H]+

후처리

  1. concentrationThe reaction solution was then concentrated
  2. washthe residue was washed with water
  3. extractionextracted with EtOAc
  4. concentrationThe organic layer was concentrated

출처 및 근거

ORD 기록
ord-b0b27a5908574f78bd916666be73e773
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08906900B2

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