Réaction #700992

ord-688987e079c14aa79c05574a501941a9

Équation de réaction

O=C([O-])O.[Na+]
NaHCO3
O=C(Cl)CI
iodoacetyl chloride
NC(=O)c1cc(N)ccc1O
5-Aminosalicylamide
→
NC(=O)c1cc(NC(=O)CI)ccc1O
5-(iodoacetamido)salicylamide
Rendement 96.0%

Réactifs

O=C([O-])O.[Na+]
NaHCO3
O=C(Cl)CI
iodoacetyl chloride
—
ice
NC(=O)c1cc(N)ccc1O
5-Aminosalicylamide

Réactifs

Aucun

Solvants

O
water

Conditions de réaction

Température
2.5°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONis added dropwise over 15 min
  2. 2
    AutreThe precipitate is collected
  3. 3
    Séchagedried in vacuo over NaOH pellets

Mode opératoire

To an ice-cooled, stirred solution of 5-Aminosalicylamide (10.0 grams, 0.073 mol), in 300 mL of water containing NaHCO3 (42.0 grams, 0.5 mol), iodoacetyl chloride (18.4 grams, 0.09 mol) is added dropwise over 15 min. After stirring at 0-5° C. for 1 hr., the solution is acidified with cold 6 N HCI. The precipitate is collected and dried in vacuo over NaOH pellets, to afford 21.3 grams (96% yield) of crude 5-(iodoacetamido)salicylamide.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US06008406uspto-grants-1999_12