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Hydrochloric Acid → 4-fluoro-2-[[(4-methoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

HRID 728634
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HRID 728634 반응식
[F:1][C:2]1[C:10]2[N:9]=[C:8]([S:11][CH2:12][C:13]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][N:14]=3)[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([O-])(O)=[O:22].[Na+].ClC1C=CC=C(C(OO)=O)C=1.[OH-].[Na+].Cl>C(Cl)Cl.O>[F:1][C:2]1[C:10]2[N:9]=[C:8]([S:11]([CH2:12][C:13]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][N:14]=3)=[O:22])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1
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참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 156624884-Fluoro-2-[[(4-methoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole

생성물 1

HCID 156624894-fluoro-2-[[(4-methoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매3회

실험 절차

4-Fluoro-2[[(4-methoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole (1.31 g, 0.0045 mol) was dissolved in methylene chloride (60 ml). NaHCO3 (0.76 g, 0.0090 mol) dissolved in water (10 ml) was added and the mixture was cooled to +2° C. m-Chloroperbenzoic acid, 84% (1.64 g, 0.0045 mol) dissolved in methylene chloride (10 ml) was added dropwise with stirring. Stirring was continued at +2° C. for 15 min. After separation the organic layer was extracted with an aqueous 0.20 M NaOH solution (2×25 ml, 0.010 mol). The combined aqueous solutions were neutralized to pH 7-8 with 0.1 M HCl in the presence of methylene chloride [100 ml). After separation the aqueous layer was extracted with methylene chloride and the combined organic solutions were dried over MgSO4. The solutions was evaporated and the title compound was obtained (1.06 g, 77%). NMR data for the final product is given below.

후처리

  1. additionwas added
  2. additionwas added dropwise
  3. stirringStirring
  4. customAfter separation the organic layer
  5. customAfter separation the aqueous layer
  6. extractionwas extracted with methylene chloride
  7. dry with materialthe combined organic solutions were dried over MgSO4
  8. customThe solutions was evaporated

출처 및 근거

ORD 기록
ord-8ca408083d59442c8d50ba8982284686
출처 데이터셋
uspto-grants-1991_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05049674

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