Reaktion #1700606

ord-4732c0f0ec0140cabcee4979217d1089

Reaktionsgleichung

CCN(CC)CC
triethylamine
NS(=O)(=O)Cl
sulfamoyl chloride
CCN(CC)CC
triethylamine
Oc1cccc(-n2ccnc2)c1
3(1H-imidazol-1-yl)phenol
NS(=O)(=O)Cl
sulfamoyl chloride
O=C=NS(=O)(=O)Cl
chlorosulfonyl isocyanate
→
NS(=O)(=O)Oc1cccc(-n2ccnc2)c1
Sulfamic acid 3-(1H-imidazol-1-yl)phenyl ester

Edukte

CCN(CC)CC
triethylamine
NS(=O)(=O)Cl
sulfamoyl chloride
CCN(CC)CC
triethylamine
Oc1cccc(-n2ccnc2)c1
3(1H-imidazol-1-yl)phenol
NS(=O)(=O)Cl
sulfamoyl chloride
O=C=NS(=O)(=O)Cl
chlorosulfonyl isocyanate

Reagenzien

Keine

Lösungsmittel

CC#N
acetonitrile

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

A solution of 3(1H-imidazol-1-yl)phenol (8 g, 0.05 mole) in acetonitrile was treated in an ice bath with sulfamoyl chloride generated from 0.075 mole of chlorosulfonyl isocyanate (Preparation 19) followed by 0.075 mole of triethylamine. After stirring overnight at room temperature, TLC, and 1H NMR of a sample showed starting material still present. The reaction was then treated with another 0.075 mole each of sulfamoyl chloride and triethylamine for another night.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05192785uspto-grants-1993_03