Hydrochloric Acid → HCID 53920798, compound

HRID 1378640Notes

Reaction equation

HRID 1378640 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].Cl>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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 3084680Iodoacetyl chlorideHCID 123251865-Amino-2-hydroxybenzamide

Product 1

HCID 53920798HCID 53920798, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 6N HCl. 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-6c2d53ead4e54704a40d690e5b9192ca
Source dataset
uspto-grants-1997_09
Patent number
US05668257

Reaction notes

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