Sodium Hydroxide → 2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethanesulfonic acid phenyl ester

HRID 1747340

Reaction equation

HRID 1747340 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:22]1([O:28][S:29]([CH:32]=[CH2:33])(=[O:31])=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[OH-].[Na+].[NH4+].[Cl-]>C1COCC1.O>[C:22]1([O:28][S:29]([CH2:32][CH2:33][N:14]2[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:12]([CH2:11][C:9]3[C:10]4[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=4[S:7][CH:8]=3)[C:13]2=[O:21])(=[O:31])=[O:30])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 564920Phenyl ethenesulfonateHCID 594973791-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

Product 1

HCID 594973292-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethanesulfonic acid phenyl esterYield 75%

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) are added Ethenesulfonic acid phenyl ester (63 mg, 0.34 mmol) and solid NaOH (14 mg, 0.34 mmol). The resulting suspension is stirred at room temperature for 0.5 hr and it turned into clear solution in about 10 min. Then saturated NH4Cl solution (5.0 mL) is added along with water (5 mL). 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 using EtOAc in Hexanes (from 0% to 30%) affords 61 mg (75%) of 2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethanesulfonic acid phenyl ester. LCMS (ESMS): m/z 479.11 (M+H+).

Workup

  1. waitit turned into clear solution in about 10 min
  2. extractionThe mixture is extracted with EtOAc (3×20 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give crude product
  6. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-aba541680b264681bd3d75ba0404740a
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Linked notes

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