Acetic Acid → Methyl (3-methyl-5-(4-aminophenoxy)-benzimidazol-2-yl)carbamate

HRID 1294063ノート

反応式

HRID 1294063 の反応式
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[O:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1.[CH3:20][O:21][C:22]([NH:24][C:25](=NC(OC)=O)SC)=[O:23].CC(O)=O>CO.[Pd]>[CH3:1][N:2]1[C:3]2[CH:4]=[C:5]([O:6][C:7]3[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=3)[CH:14]=[CH:15][C:16]=2[N:17]=[C:25]1[NH:24][C:22](=[O:23])[O:21][CH3:20]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 177559824-(3-Methylamino-4-nitrophenoxy)aniline2 回

生成物 1

HCID 17755983Methyl (3-methyl-5-(4-aminophenoxy)-benzimidazol-2-yl)carbamate収率 85%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
85 °C

実験手順

After hydrogenation of 4-(3-methylamino-4-nitrophenoxy)aniline (Intermediate 8G-519.2 mg, 2.0 mmol) with 5% Pd—C in MeOH (20 mL), 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (1.03 g, 5.0 mmol) and AcOH (2.0 mL) was added then stirred at 85° C. for 5.5 hrs. After cooling, the mixture was added 2N HClaq. (25 mL) then stirred at 65° C. for 2 hrs. The mixture was passed through celite pad to remove catalyst and the solvent was removed by evaporation. The residue was extracted with ethyl acetate. The organic layer was washed with NH4OH(aq). and brine, dried over Na2SO4 then evaporated. Sequence purification on SiO2 column chromatography gave the title compound (529.1 mg, 85%): MS m/e 313 (M+1).

後処理

  1. temperatureAfter cooling
  2. additionthe mixture was added 2N HClaq
  3. stirring(25 mL) then stirred at 65° C. for 2 hrs
  4. customto remove catalyst
  5. customthe solvent was removed by evaporation
  6. extractionThe residue was extracted with ethyl acetate
  7. washThe organic layer was washed with NH4OH(aq)
  8. dry with materialand brine, dried over Na2SO4
  9. customthen evaporated
  10. customSequence purification on SiO2 column chromatography

出典と根拠

ORDレコード
ord-2d50fc364c034066bba52de72684b015
出典データセット
uspto-grants-2007_07
特許番号
US07238813B2

反応ノート

読み込み中…