Sodium Hydroxide → HCID 25123225, compound

HRID 1747424Notes

Reaction equation

HRID 1747424 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[NH:14][C:13]3=[O:21])=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C[O:23][S:24]([CH:27]=[CH:28][CH2:29][CH2:30][CH3:31])(=[O:26])=[O:25].[OH-].[Na+].[NH4+].[Cl-]>C1COCC1.O>[CH3:1][C:2]1[C:10]2[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[N:14]([CH:28]([CH2:29][CH2:30][CH3:31])[CH2:27][S:24]([OH:26])(=[O:25])=[O:23])[C:13]3=[O:21])=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 594973791-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-oneHCID 76785645HCID 76785645, compound

Product 1

HCID 25123225HCID 25123225, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (50 mg, 0.17 mmol) in THF (1.0 mL) arc added Pent-1-ene-1-sulfonic acid methyl ester (56 mg, 0.34 mmol) and solid NaOH (14 mg, 0.34 mmol) in order. The resulting suspension is stirred at room temperature for 1 hr and it turned into a clear solution. Then 5 mL of sat.NH4Cl is added along with 5 mL of water. The mixture is extracted with EtOAc (3×20 mL). The organic layers are combined, dried (MgSO4) and concentrated to give crude product. Purification by flash column chromatography affords 11 mg (15%) of 2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentane-1-sulfonic acid. LCMS (ESMS): m/z 445.13 (M+H+).

Workup

  1. extractionThe mixture is extracted with EtOAc (3×20 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto give crude product
  5. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-989129303aa045f68acec4cabc039cc9
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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