Water → 5-(2-Hydroxy-4-nitroanilinocarbonyl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74216

反応式

HRID 74216 の反応式
Cl.[CH3:2][C:3]1[N:7]([CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:6]2[CH:14]=[CH:15][C:16]([C:18]([OH:20])=O)=[CH:17][C:5]=2[N:4]=1.S(Cl)(Cl)=O.O[C:26]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][C:27]=1N.C([N:38](CC)CC)C.[OH2:43]>C1(C)C=CC=CC=1.CN(C=O)C.O1CCCC1>[OH:43][C:27]1[CH:29]=[C:30]([N+:33]([O-:35])=[O:34])[CH:31]=[CH:32][C:26]=1[NH:38][C:18]([C:16]1[CH:15]=[CH:14][C:6]2[N:7]([CH:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[C:3]([CH3:2])=[N:4][C:5]=2[CH:17]=1)=[O:20]

参加物

9

反応物 5

HCID 962WaterHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 36133892-Amino-4-NitrophenolHCID 674984452-methyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid HCl salt

生成物 1

HCID 674981775-(2-Hydroxy-4-nitroanilinocarbonyl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole収率 17.1%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 2-methyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid HCl salt (see Working Example 4-3) (0.75 g, 2.9 mmol) in toluene (10 mL) containing DMF (1 drop) was added thionyl chloride (0.41 g, 3.4 mmol), and this was refluxed for 7 hours with stirring. After the reaction was complete, concentration at reduced pressure gave a residue that was added to 2-hydroxy-5-nitroaniline (0.44 g, 2.9 mmol), triethylamine (0.32 g, 3.2 mmol) and tetrahydrofuran (5 mL), and this was stirred at room temperature for 3 hours. After the reaction was complete, water (30 mL) was added and the precipitated crystals were filtered off. After the crystals were washed with water, they were dried with heating at reduced pressure to yield the title compound (195 mg, 17.1%) as a light brown solid.

後処理

  1. temperaturethis was refluxed for 7 hours
  2. concentrationconcentration at reduced pressure
  3. customgave a residue that
  4. stirringthis was stirred at room temperature for 3 hours
  5. filtrationthe precipitated crystals were filtered off
  6. washAfter the crystals were washed with water, they
  7. customwere dried
  8. temperaturewith heating at reduced pressure

出典と根拠

ORDレコード
ord-0d156a25ad514904a3cdcd09accb1945
出典データセット
uspto-grants-2014_09
特許番号
US08829035B2

関連ノート

読み込み中…