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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
Notes
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Reaction equation

HRID 1747342 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 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

Product 1

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

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-f292c58bf2ec4f9aaadaed2d4b891af3
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09150556B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes