Trifluoromethanesulfonic acid → 1-Benzyl-1H-benzo[d]imidazol-2(3H)-one

HRID 602583노트

반응식

HRID 602583 반응식
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10](/C(/C)=C\SC)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.O.C(S(O)(=O)=O)(F)(F)F>O>[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][C:9]1=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 62406Trifluoromethanesulfonic acidHCID 22242641Methanol--water (1/1)HCID 462035751-benzyl-3-[(1Z)-1-(methylsulfanyl)prop-1-en-2-yl]-1,3-dihydro-2H-benzimidazol-2-one

생성물 1

HCID 7365051-Benzyl-1H-benzo[d]imidazol-2(3H)-one수율 48%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

35 mg of 1-benzyl-3-[(1Z)-1-(methylsulfanyl)prop-1-en-2-yl]-1,3-dihydro-2H-benzimidazol-2-one 1 (0.113 mmol) prepared as described in example 2 were solubilised in a solution of MeOH/H2O 1:1 (2 mL). Then, CF3SO3H (2 mL) was added and the solution refluxed under magnetic stirring. After 3 h, H2O was added (5 mL) and the solution was extracted 3×10 mL of CH2Cl2. The resulting solid was finally chromatographed on silica gel (CH2Cl2/AcOEt 8:2) to yield 1-benzyl-1,3-dihydro-2H-benzimidazol-2-one 2 as a white powder (12 mg, 48%). Mp 194° C. (Iitt. G. Vernin, H. Domlog, C. Siv, J. Metzger, J. Heterocyclic Chem., 18, 85 (1981): 198° C.); Rf=0.23 (CH2Cl2/AcOEt 8:2); 1H NMR (200 MHz, CDCl3) δ=5.11 (2H, s, CH2), 6.84-7.35 (9H, m, Ar), 10.08 (1H, brs, NH).

후처리

  1. temperaturethe solution refluxed under magnetic stirring
  2. extractionthe solution was extracted 3×10 mL of CH2Cl2
  3. customThe resulting solid was finally chromatographed on silica gel (CH2Cl2/AcOEt 8:2)

출처 및 근거

ORD 기록
ord-e4f54656b7ec4230b37b7e16382a9728
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906541B2

반응 노트

불러오는 중…