Sodium Bicarbonate → 1-Ethoxycarbonyl-2-(4-methoxy-2-picolylsulfinyl)-1H-thieno[3,4-d]imidazole

HRID 231158Notes

Reaction equation

HRID 231158 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:10]2=[CH:11][S:12][CH:13]=[C:9]2[N:8]=[C:7]1[S:14][CH2:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][N:17]=1)=[O:5])[CH3:2].C(=O)(O)[O-:25].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]1[C:10]2=[CH:11][S:12][CH:13]=[C:9]2[N:8]=[C:7]1[S:14]([CH2:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][N:17]=1)=[O:25])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 141543241-Ethoxycarbonyl-2-(4-methoxy-2-picolylmercapto)-1H-thieno[3,4-d]imidazole

Product 1

HCID 141543581-Ethoxycarbonyl-2-(4-methoxy-2-picolylsulfinyl)-1H-thieno[3,4-d]imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 750 mg (2.1 mmol) of 1-ethoxycarbonyl-2-(4-methoxy-2-picolylmercapto)-1H-thieno[3,4-d]imidazole in 30 ml of methylene chloride and 25 ml of 0.5 N aqueous sodium bicarbonate solution were added dropwise, with stirring, initially 420 mg (2.1 mmol) and then a further 210 mg (1.05 mmol) of 3-chloroperbenzoic acid CH2Cl2. The organic phase was dried over MgSO4 and concentrated in vacuo, and the residue was crystallized from ethyl acetate. Melting point 143° C. (decomposition).

Workup

  1. dry with materialThe organic phase was dried over MgSO4
  2. concentrationconcentrated in vacuo
  3. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-5b97ff36f07c423f9afd8651b883a67a
Source dataset
uspto-grants-1989_07
Patent number
US04845118

Reaction notes

Loading…