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Methyl formate → 5-Carbomethoxy-6-methyl-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

HRID 1647150
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HRID 1647150 반응식
[C:1]([C:5]1[C:25]([CH3:26])=[CH:24][C:8]2[NH:9][C:10]([S:12][CH2:13][C:14]3[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[CH:16][N:15]=3)=[N:11][C:7]=2[CH:6]=1)([O:3][CH3:4])=[O:2].C([O-])(O)=[O:28].[Na+].ClC1C=CC=C(C(OO)=O)C=1.[OH-].[Na+].C(OC)=O>C(Cl)Cl.O>[C:1]([C:5]1[C:25]([CH3:26])=[CH:24][C:8]2[NH:9][C:10]([S:12]([CH2:13][C:14]3[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[CH:16][N:15]=3)=[O:28])=[N:11][C:7]=2[CH:6]=1)([O:3][CH3:4])=[O:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 7865Methyl formateHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 218515495-Carbomethoxy-6-methyl-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole

생성물 1

HCID 98651425-Carbomethoxy-6-methyl-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole
수율 70%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매3회

실험 절차

5--Carbomethoxy-6-methyl-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole (1.03 g, 0.00276 mol) was dissolved in CH2Cl2 (30 ml). NaHCO3 (0.46 g, 0.0055 mol) in H2O (10 ml) was added and the mixture was cooled to +2° C. m-chloroperbenzoic acid 69.5% (0.62 g, 0.0025 mol) dissolved in CH2Cl2 (5 ml) was added dropwise under stirring. Stirring was continued at +2° C. for 15 min. After separation the organic layer was extracted with an aqueous 0.2M NaOH solution (3×15 ml, 0.009 mol). After separation the aqueous solutions were combined and neutralized with methyl formate (0.56 ml, 0.009 mol) in the presence of CH2Cl2 (25 ml). After separation the organic layer was dried over Na2SO4 and evaporated under reduced pressure. The residue was crystallized from CH3CN (10 ml) giving the title compound (0.68 g, 70%).

후처리

  1. additionwas added dropwise
  2. stirringStirring
  3. customAfter separation the organic layer
  4. customAfter separation the aqueous solutions
  5. customAfter separation the organic layer
  6. dry with materialwas dried over Na2SO4
  7. customevaporated under reduced pressure
  8. customThe residue was crystallized from CH3CN (10 ml)

출처 및 근거

ORD 기록
ord-56cbb2624580496596adb4d261fdd9b4
출처 데이터셋
uspto-grants-1995_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05430042

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