m-Chloroperbenzoic acid → HCID 178468687, compound

HRID 1647152Notes

Reaction equation

HRID 1647152 reaction equation
[C:1]([C:6]1[CH:26]=[CH:25][C:9]2[NH:10][C:11]([S:13][CH2:14][C:15]3[C:20]([O:21][CH3:22])=[C:19]([O:23][CH3:24])[CH:18]=[CH:17][N:16]=3)=[N:12][C:8]=2[CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2].C([O-])(O)=[O:28].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl.O>[C:1]([C:6]1[CH:26]=[CH:25][C:9]2[NH:10][C:11]([S:13]([CH2:14][C:15]3[C:20]([O:21][CH3:22])=[C:19]([O:23][CH3:24])[CH:18]=[CH:17][N:16]=3)=[O:28])=[N:12][C:8]=2[CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 178468685HCID 178468685, compound

Product 1

HCID 178468687HCID 178468687, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

5--Carbethoxy-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole (95.2% pure) (1.4 g, 0.0036 mol) was dissolved in CH2Cl2 (30 ml). NaHCO3 (0.6 g, 0.0072 mol in H2O (10 ml) was added and the mixture was cooled to +2° C. m-Chloroperbenzoic acid 69.5% (0.87 g, 0.0035 mol) dissolved in CH2Cl2 (5 ml) was added dropwise under stirring. Stirring was continued at +2° C. for 10 min. The phases were separated and the organic phase was dried over Na2SO4 and evaporated under reduced pressure. The residue was crystallized from CH3CN (15 ml ) giving the title compound (0.76 g, 54%).

Workup

  1. additionwas added dropwise
  2. stirringStirring
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe residue was crystallized from CH3CN (15 ml )

Sources & evidence

ORD record
ord-9e2e3d4567eb45fe8612f9660434e854
Source dataset
uspto-grants-1995_07
Patent number
US05430042

Reaction notes

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