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

Reaktionsgleichung

Reaktionsgleichung von HRID 1747340
[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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-aba541680b264681bd3d75ba0404740a
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150556B2

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