Sodium Thiosulfate → 2-amino-6-ethylsulfonyl-1H-benzoimidazole-4-carboxylic acid ethyl ester

HRID 1367997Notes

Reaction equation

HRID 1367997 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[N:13]=[C:12]([NH2:15])[NH:11][C:10]=2[CH:9]=[C:8](SCC)[CH:7]=1)=[O:5])[CH3:2].[CH:19]1C=C(Cl)C=C(C(OO)=O)[CH:20]=1.C([O-])(O)=O.[Na+].[O-:35][S:36]([O-:39])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[N:13]=[C:12]([NH2:15])[NH:11][C:10]=2[CH:9]=[C:8]([S:36]([CH2:19][CH3:20])(=[O:39])=[O:35])[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 669408182-amino-6-ethylsulfanyl-1H-benzoimidazole-4-carboxylic acid ethyl ester

Product 1

HCID 669405312-amino-6-ethylsulfonyl-1H-benzoimidazole-4-carboxylic acid ethyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.26 g (1.0 mmol) of 2-amino-6-ethylsulfanyl-1H-benzoimidazole-4-carboxylic acid ethyl ester (See Example 489) in DCM was stirred with 0.35 g (2.0 mmol) of MCPBA and 0.34 g (4.0 mmol) of NaHCO3 at room temperature for 3 h. The reaction mixture was treated with Na2S2O3 solution and stirred for 0.5 h at room temperature. EtOAc extraction, followed by washing with dilute NaOH solution and brine, and evaporation of the solvent produced 0.28 g (0.94 mmol, 94%) of 2-amino-6-ethylsulfonyl-1H-benzoimidazole-4-carboxylic acid ethyl ester. LCMS: 298 (M+1)+.

Workup

  1. extractionEtOAc extraction
  2. washby washing with dilute NaOH solution and brine, and evaporation of the solvent

Sources & evidence

ORD record
ord-b902b2668fac4f0d9ea1a054dc45b6ef
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

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