Sodium Bicarbonate → HCID 53920798, compound

HRID 613810Notes

Reaction equation

HRID 613810 reaction equation
[NH2:1][C:2]1[CH:10]=[C:6]([C:7]([NH2:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[I:17][CH2:18][C:19](Cl)=[O:20]>O>[I:17][CH2:18][C:19]([NH:1][C:2]1[CH:10]=[C:6]([C:7]([NH2:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1)=[O:20]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 3084680Iodoacetyl chlorideHCID 123251865-Amino-2-hydroxybenzamide

Product 1

HCID 53920798HCID 53920798, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

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.

Workup

  1. additionis added dropwise over 15 min
  2. customThe precipitate is collected
  3. dry with materialdried in vacuo over NaOH pellets

Sources & evidence

ORD record
ord-688987e079c14aa79c05574a501941a9
Source dataset
uspto-grants-1999_12
Patent number
US06008406

Reaction notes

Loading…