Hydrochloric Acid → HCID 118963265, compound

HRID 2420467Notes

Reaction equation

HRID 2420467 reaction equation
C([C@@:3]([C:22]([OH:24])=[O:23])([CH2:5][C:6]1[CH:11]=[C:10]([I:12])[C:9]([O:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[C:8]([I:21])[CH:7]=1)N)C.[CH2:25]([NH2:27])[CH3:26].[I-:28].[K+].[I:30]I.Cl>O>[CH2:25]([NH:27][C@H:3]([C:22]([OH:24])=[O:23])[CH2:5][C:6]1[CH:11]=[C:10]([I:12])[C:9]([O:13][C:14]2[CH:19]=[C:18]([I:30])[C:17]([OH:20])=[C:16]([I:28])[CH:15]=2)=[C:8]([I:21])[CH:7]=1)[CH3:26]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 4875Potassium IodideHCID 6341EthylamineHCID 53735156HCID 53735156, compound

Product 1

HCID 118963265HCID 118963265, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

22.1 g. of α-ethyl-3,5-di-iodo thyronine are dissolved in 130 cc. of a 33% solution of ethylamine in water and 86.5 cc. of a 1.85 N solution of potassium iodide and iodine are added drop by drop to the above described solution while stirring. Stirring is continued for one more hour and 16% hydrochloric acid is added in an amount sufficient to adjust the pH value to a pH of 5.0. The precipitate is filtered off, washed with water, and dissolved in 250 cc. of ethanol with the addition of 100 cc. of 2 N sodium hydroxide solution. The solution is purified by means of charcoal and is acidified with 2 N hydrochloric acid to a pH of 6.0. α-Ethyl thyroxine, melting at 236°-238° C. is obtained in a yield of 60% of the theoretical yield.

Workup

  1. stirringStirring
  2. additionis added in an amount sufficient
  3. filtrationThe precipitate is filtered off
  4. washwashed with water
  5. dissolutiondissolved in 250 cc
  6. additionof ethanol with the addition of 100 cc
  7. customThe solution is purified by means of charcoal

Sources & evidence

ORD record
ord-037a7aef609947d6a1d40a5fa3a1260e
Source dataset
uspto-grants-1978_08
Patent number
US04110470

Reaction notes

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