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

HRID 1294060
ノート
印刷プレビュー

反応式

HRID 1294060 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 17755333N-Methyl-4-(4-nitrophenoxy)-2-nitroaniline2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a226441c0c6e4a14bc2bb4b2c4e62e57
出典データセット
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07238813B2

反応ノート

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