Reaktion #78497

ord-61cb77a36a7849aab9f189feb32228c2

Reaktionsgleichung

CCOC(=O)CCN(C(=O)c1ccc2sc(CSc3ccc(C#N)cc3)nc2c1)c1ccccc1
2-[(4-cyanophenyl)thiomethyl]benzothiazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide
Cl
hydrochloric acid
CCO
ethanol
O=C([O-])[O-].[NH4+].[NH4+]
ammonium carbonate
→
CCOC(=O)CCN(C(=O)c1ccc2sc(CSc3ccc(C(=N)N)cc3)nc2c1)c1ccccc1.Cl
2-[(4-amidinophenyl)thiomethyl]benzothiazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide hydrochloride
Ausbeute 61.0%

Edukte

CCOC(=O)CCN(C(=O)c1ccc2sc(CSc3ccc(C#N)cc3)nc2c1)c1ccccc1
2-[(4-cyanophenyl)thiomethyl]benzothiazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide
Cl
hydrochloric acid
CCO
ethanol
O=C([O-])[O-].[NH4+].[NH4+]
ammonium carbonate
—
C27H26N4O3S2

Reagenzien

CC(=O)O
acetic acid

Lösungsmittel

CCO.ClCCl
methylene chloride ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Prepared analogously to Example 9 from 2-[(4-cyanophenyl)thiomethyl]benzothiazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide, ethanolic hydrochloric acid, ethanol, and ammonium carbonate. Yield: 61% of theory, C27H26N4O3S2 (518.66); Rf value: 0.27 (silica gel; methylene chloride/ethanol=4:1+a few drops of acetic acid); EKA mass spectrum: (M+H)+=519.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06710055B2uspto-grants-2004_03