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Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamate → Methyl (1-methyl-5-(4-aminophenoxy)-benzimidazol-2-yl)carbamate

HRID 1294060
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HRID 1294060 반응식
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)=[CH:5][C:4]=1[N+:19]([O-])=O.[CH3:22][O:23][C:24]([NH:26][C:27](=NC(OC)=O)SC)=[O:25]>CO.[Pd]>[CH3:1][N:2]1[C:3]2[CH:8]=[CH:7][C:6]([O:9][C:10]3[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=3)=[CH:5][C:4]=2[N:19]=[C:27]1[NH:26][C:24](=[O:25])[O:23][CH3:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 17755333N-Methyl-4-(4-nitrophenoxy)-2-nitroaniline2회

생성물 1

HCID 17755417Methyl (1-methyl-5-(4-aminophenoxy)-benzimidazol-2-yl)carbamate수율 12.3%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

To a mixture of N-methyl-4-(4-nitrophenoxy)-2-nitroaniline (Intermediate 8B -2.10 g, 2.27 mmol) in MeOH (100 mL) was added 5% Pd—C (catalytic amount) and stirred at room temperature under H2 atmosphere. After 7 hrs, the catalyst was removed by filtration then the solvent was evaporated off. The residual mixture was dissolved into MeOH (50 mL) and added 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (3.0 g, 14.5 mmol). The mixture was refluxed overnight. The solvent was removed by evaporation and sequence purification on SiO2 column chromatography gave title compound (87.3 mg, 4%): MS m/e 313 (M+1).

후처리

  1. customthe catalyst was removed by filtration
  2. customthe solvent was evaporated off
  3. dissolutionThe residual mixture was dissolved into MeOH (50 mL)
  4. temperatureThe mixture was refluxed overnight
  5. customThe solvent was removed by evaporation and sequence purification on SiO2 column chromatography

출처 및 근거

ORD 기록
ord-a226441c0c6e4a14bc2bb4b2c4e62e57
출처 데이터셋
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07238813B2

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