p-Toluenesulfonic acid monohydrate → 2-Methyl-5-(6-nitrobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74217노트

반응식

HRID 74217 반응식
O[C:2]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:3]=1[NH:4][C:5]([C:7]1[CH:22]=[CH:21][C:10]2[N:11]([CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[C:12]([CH3:14])=[N:13][C:9]=2[CH:8]=1)=[O:6].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:14][C:12]1[N:11]([CH:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[C:10]2[CH:21]=[CH:22][C:7]([C:5]3[O:6][C:2]4[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:3]=4[N:4]=3)=[CH:8][C:9]=2[N:13]=1

참가 물질

4

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 674981775-(2-Hydroxy-4-nitroanilinocarbonyl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole

생성물 1

HCID 674986292-Methyl-5-(6-nitrobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole수율 77.4%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

5-(2-Hydroxy-4-nitroanilinocarbonyl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole (see Working Example 47-1) (195 mg, 0.492 mmol) was added to toluene (20 mL), after which p-toluenesulfonic acid hydrate (280 mg, 1.47 mmol) was added and this was refluxed with stirring for 4 hours. After the solvent was concentrated under reduced pressure, a sodium bicarbonate water (10 mL) was added and this was stirred at room temperature for 1 hour. The precipitated crystals were filtered off, and after being washed with water were dried with heating at reduced pressure to yield the title compound (144 mg, 77.4% yield) as a pale yellow solid.

후처리

  1. temperaturethis was refluxed
  2. concentrationAfter the solvent was concentrated under reduced pressure
  3. additiona sodium bicarbonate water (10 mL) was added
  4. stirringthis was stirred at room temperature for 1 hour
  5. filtrationThe precipitated crystals were filtered off
  6. washafter being washed with water
  7. customwere dried
  8. temperaturewith heating at reduced pressure

출처 및 근거

ORD 기록
ord-4fa43155368946e4ae3c37185c3491d2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

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