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

HRID 1647150
Notes
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Reaction equation

HRID 1647150 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 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

Product 1

HCID 9865142
5-Carbomethoxy-6-methyl-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole
Yield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-56cbb2624580496596adb4d261fdd9b4
Source dataset
uspto-grants-1995_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05430042

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes