Iodine → HCID 70560461, compound

HRID 126961Notes

Reaction equation

HRID 126961 reaction equation
[C:1]([C:11]1[C:12]([OH:23])=[C:13](CN)[C:14]2[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=2[CH:20]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH2:24]([NH2:27])CN.[I:28]I.[I-].[K+]>C(O)C.O>[I:28][C:13]1[C:14]2[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=2[C:20]([CH2:24][NH2:27])=[C:11]([C:1]([O:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:2])[C:12]=1[OH:23]

Participants

7

Reactant 4

HCID 807IodineHCID 3301EthylenediamineHCID 4875Potassium IodideHCID 70560444HCID 70560444, compound

Product 1

HCID 70560461HCID 70560461, compoundYield 108.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

In 750 ml of ethanol was dissolved 50 g of the compound (4) under heating, and 7.5 g (8.35 L ml) of ethylenediamine was added to the solution. A mixture of 50.8 g of iodine and 41.5 g of potassium iodide was dissolved in 500 ml of water, and the resulting aqueous solution was added dropwise to the previously prepared solution over about 30 minutes under stirring at 30° C. After additional 1 hour`s stirring, the precipitating solid was filtered off, which was washed with 50% ethanol, and dried to provide 59 g of the title compound (5) having the following physical properties.

Workup

  1. temperatureunder heating
  2. additionthe resulting aqueous solution was added dropwise to the previously prepared solution over about 30 minutes
  3. stirringAfter additional 1 hour`s stirring
  4. filtrationthe precipitating solid was filtered off
  5. washwhich was washed with 50% ethanol
  6. customdried

Sources & evidence

ORD record
ord-bf917ef66fa4444aab3956cde99aa3f8
Source dataset
uspto-grants-1981_03
Patent number
US04254056

Reaction notes

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