Ethyl Acetate → 4-Iodo-5-methyl-1H-benzoimidazole

HRID 723235노트

반응식

HRID 723235 반응식
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]2[NH:6][CH:7]=[N:8][C:4]=2[CH:3]=1.C1C(=O)N([I:18])C(=O)C1.CCOC(C)=O.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O>[I:18][C:3]1[C:4]2[N:8]=[CH:7][NH:6][C:5]=2[CH:9]=[CH:10][C:2]=1[CH3:1]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 119795-MethylbenzimidazoleHCID 120273N-IodosuccinimideHCID 516892Sodium Bicarbonate

생성물 1

HCID 218863944-Iodo-5-methyl-1H-benzoimidazole수율 30.2%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

A solution of 5-methyl-1H-benzoimidazole (132 mg, 1.0 mmol) and NIS (248 mg, 1.10 mmol) in 1 mL of TFA was reflux for 1 hr and then cooled to RT. Treated with 30 mL of EtOAc, the mixture was neutralized with sat. NaHCO3 solution. The organic layer was washed with H2O (10 mL), brine (10 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (5% MeOH/CH2Cl2) gave 78 mg (30%) of product as a white solid: 1H-NMR (CDCl3; 400 MHz) δ 8.07 (d, 1H), 7.57 (br s, 1H), 7.22 (d, 1H, J. 8.4 Hz), 2.59 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C8H7IN2, 259.0 (M+H), found 259.2.

후처리

  1. washThe organic layer was washed with H2O (10 mL), brine (10 mL)
  2. dry with materialdried (Na2SO4)
  3. customRemoval of the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-ac87af7ff7c34219a70567ee909e8579
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138530B2

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