Hydrochloric Acid → HCID 53920798, compound

HRID 2294513Notes

Reaction equation

HRID 2294513 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-4f89c4342af0440b817e90fc09911820
Source dataset
uspto-grants-1997_11
Patent number
US05688928

Reaction notes

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