Hydrogen Peroxide → HCID 18412562, compound

HRID 50331Notes

Reaction equation

HRID 50331 reaction equation
[ClH:1].[C:2]1([N:8]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:9]([C:11]2[CH:12]=[CH:13][C:14]3[S:18][C:17]([CH2:19][S:20][C:21]4[CH:26]=[CH:25][C:24]([C:27](=[NH:29])[NH2:28])=[CH:23][CH:22]=4)=[N:16][C:15]=3[CH:30]=2)=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:38]O>C(O)(=O)C>[ClH:1].[C:2]1([N:8]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:9]([C:11]2[CH:12]=[CH:13][C:14]3[S:18][C:17]([CH2:19][S:20]([C:21]4[CH:26]=[CH:25][C:24]([C:27](=[NH:28])[NH2:29])=[CH:23][CH:22]=4)=[O:38])=[N:16][C:15]=3[CH:30]=2)=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 18412290HCID 18412290, compound

Product 1

HCID 18412562HCID 18412562, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 0.15 g (0.27 mmol) of 2-[(4-amidinophenyl)thiomethyl]benzothiazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide hydrochloride in 10 mL of acetic acid was mixed with 0.09 mL (about 0.81 mmol) of 30% hydrogen peroxide solution and stirred at room temperature. After 4 days, a further 0.18 mL of hydrogen peroxide solution was added and the resulting mixture was stirred for a further two days. After removal of the solvent in vacuo, the crude product obtained was purified by flash chromatography (silica gel; methylene chloride/ethanol=10:1 to 4:1). Yield: 58% of theory, C27H26N4O4S2 (534.66); Rf value: 0.24 (silica gel; methylene chloride/ethanol=4:1+a few drops of acetic acid); EKA mass spectrum: (M+H)+=535.

Workup

  1. stirringthe resulting mixture was stirred for a further two days
  2. customAfter removal of the solvent in vacuo

Sources & evidence

ORD record
ord-aceb74443d4e4713904823d5766d8541
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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