Methyl formate → HCID 178493211, compound

HRID 1089119Notes

Reaction equation

HRID 1089119 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[NH:6][C:7]([S:9][CH2:10][C:11]3[C:16]([O:17][CH3:18])=[C:15]([O:19][CH3:20])[CH:14]=[CH:13][N:12]=3)=[N:8][C:4]=2[CH:3]=1.C([O-])(O)=[O:24].[Na+].C1C=C(Cl)C=C(C(OO)=O)C=1.[OH-].[Na+].C(OC)=O>C(Cl)Cl.O>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[NH:6][C:7]([S:9]([CH2:10][C:11]3[C:16]([O:17][CH3:18])=[C:15]([O:19][CH3:20])[CH:14]=[CH:13][N:12]=3)=[O:24])=[N:8][C:4]=2[CH:3]=1

Participants

8

Reactant 5

HCID 7865Methyl formateHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 178493200HCID 178493200, compound

Product 1

HCID 178493211HCID 178493211, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

5-chloro-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole (645 mg, 0.0019 mol) was dissolved in 25 ml CH2Cl2 and mixed with NaHCO3 (323 mg, 0.0038 mol) dissolved in 10 ml H2O. The stirred mixture was cooled to 0° C. and treated with MCPBA (84%, 389 mg, 0.0019 mol) dissolved in 6 ml CH2Cl2. After reacting for 10 min the layers were separated and the aqueous layer extracted with 5 ml CH2Cl2. The organic layers were combined and extracted with 20 ml water containing NaOH (154 mg, 0.0038 mol). The latter aqueous layer was collected (residual CH2Cl2 distilled off on the rotavapor) and treated with two portions of HCOOCH3 (2×118 μl, 0.0038 mol).

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer extracted with 5 ml CH2Cl2
  3. extractionextracted with 20 ml water
  4. customThe latter aqueous layer was collected (residual CH2Cl2
  5. distillationdistilled off on the rotavapor) and

Sources & evidence

ORD record
ord-618440a142b24cb194409ed331439359
Source dataset
uspto-grants-1990_10
Patent number
US04965269

Reaction notes

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