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

반응식

HRID 1747340 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-aba541680b264681bd3d75ba0404740a
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150556B2

연결된 노트

불러오는 중…