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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
ノート
印刷プレビュー

反応式

HRID 1747342 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-f292c58bf2ec4f9aaadaed2d4b891af3
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09150556B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート