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

反応式

HRID 1747340 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-aba541680b264681bd3d75ba0404740a
出典データセット
uspto-grants-2015_10
特許番号
US09150556B2

関連ノート

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