Hydrochloric Acid → 2-[N-(4-amidinophenyl)aminomethyl]benzothiazole-5-carboxylic acid-N-phenvl-N-(2-carboxyethyl)amide

HRID 2227631Notes

Reaction equation

HRID 2227631 reaction equation
[C:1]1([N:7]([CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])[C:8]([C:10]2[CH:11]=[CH:12][C:13]3[S:17][C:16]([CH2:18][NH:19][C:20]4[CH:25]=[CH:24][C:23]([C:26](=[NH:28])[NH2:27])=[CH:22][CH:21]=4)=[N:15][C:14]=3[CH:29]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>C(O)C.ClCCl.C(O)C>[C:1]1([N:7]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])[C:8]([C:10]2[CH:11]=[CH:12][C:13]3[S:17][C:16]([CH2:18][NH:19][C:20]4[CH:25]=[CH:24][C:23]([C:26](=[NH:27])[NH2:28])=[CH:22][CH:21]=4)=[N:15][C:14]=3[CH:29]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 184123862-[N-(4-amidinophenyl)aminomethyl]benzothiazole-5-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

Product 1

HCID 154332162-[N-(4-amidinophenyl)aminomethyl]benzothiazole-5-carboxylic acid-N-phenvl-N-(2-carboxyethyl)amide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

0.45 g (0.84 mmol) of 2-[N-(4-amidinophenyl)aminomethyl]benzothiazole-5-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide were dissolved in 15 ml of ethanol, mixed with 2 ml of 2N sodium hydroxide solution, and stirred for 4 hours at room temperature. Then the mixture was acidified with 3 ml of 2N hydrochloric acid and the solvent was distilled off. The crude product obtained was taken up in 5 ml dichloromethane/ethanol (2:1) and filtered to remove the insoluble sodium chloride. After the distillation of the solvent, the desired compound was obtained as a yellow foam.

Workup

  1. distillationthe solvent was distilled off
  2. customThe crude product obtained
  3. filtrationfiltered
  4. customto remove the insoluble sodium chloride
  5. distillationAfter the distillation of the solvent

Sources & evidence

ORD record
ord-e5b88848089542a891ef0b5f511a2fc8
Source dataset
uspto-grants-2002_07
Patent number
US06414008B1

Reaction notes

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