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Hydrochloric Acid → 2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethanesulfonic acid

HRID 1747342
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HRID 1747342 반응식
C1([O:7][S:8]([CH2:11][CH2:12][N:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]([CH2:22][C:23]3[C:24]4[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:25]=4[S:26][CH:27]=3)[C:14]2=[O:33])(=[O:10])=[O:9])C=CC=CC=1.[OH-].[Na+].Cl.O>C(O)C.C1COCC1.CO.C(Cl)Cl>[CH3:32][C:31]1[C:24]2[C:23]([CH2:22][N:15]3[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[N:13]([CH2:12][CH2:11][S:8]([OH:10])(=[O:9])=[O:7])[C:14]3=[O:33])=[CH:27][S:26][C:25]=2[CH:28]=[CH:29][CH:30]=1
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참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 594973292-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethanesulfonic acid phenyl ester

생성물 1

HCID 594975382-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethanesulfonic acid수율 58%

시약·촉매·용매 4

HCID 702Ethanol용매HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethanesulfonic acid phenyl ester (25 mg, 0.052 mmol) is dissolved in ethanol (1.0 mL) and THF (1.0 mL), 2.0N NaOH solution (1.0 mL) is added into it and the mixture is warmed up to 80° C. for 3 hr. Then 1.0 M HCl solution (5.0 mL) is added along with water (15 mL). The mixture is extracted with EtOAc (3×35 mL) and the organic layers are combined, dried (MgSO4) and concentrated to give crude product. The crude is then dissolved in 10% MeOH in CH2Cl2 and purified by column chromatography eluting with 10% MeOH in CH2Cl2 to give 12 mg (58%) of 2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethanesulfonic acid. LCMS (ESMS): m/z 403.08 (M+H+).

후처리

  1. extractionThe mixture is extracted with EtOAc (3×35 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto give crude product
  5. custompurified by column chromatography
  6. washeluting with 10% MeOH in CH2Cl2

출처 및 근거

ORD 기록
ord-f292c58bf2ec4f9aaadaed2d4b891af3
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09150556B2

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