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

HRID 74216

반응식

HRID 74216 반응식
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]

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0d156a25ad514904a3cdcd09accb1945
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

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