Iodine → HCID 86733375, compound

HRID 973221Notes

Reaction equation

HRID 973221 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=[O:11].[NH:13]1[CH2:17][CH2:16][NH:15][C:14]1=[S:18].[I:19]I.[I-].[K+]>CO.O>[IH:19].[NH:15]1[CH2:16][CH2:17][N:13]=[C:14]1[S:18][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]=1[C:10]([OH:12])=[O:11]

Participants

7

Reactant 4

HCID 807IodineHCID 4875Potassium IodideHCID 72899Indole-2-carboxylic acidHCID 2723650Ethylenethiourea

Product 1

HCID 86733375HCID 86733375, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 3,2 g indole-2-carboxylic acid in 50 ml methanol and 2 g 2-imidazolidinethione in 100 ml methanol is added to a well-stirred solution of 3 g iodine and 25 g potassium iodide in 50 ml water. After being stirred for 2 hours at room temperature, the mixture is filtered to remove the product. The filtrate is concentrated and cooled to give further yield. The combined product is recrystallised from alcohol-ether to give 3-(2-imidazolin-2-ylthio)-indole-2-carboxylic acid hydriodide melting above 310°.

Workup

  1. filtrationthe mixture is filtered
  2. customto remove the product
  3. concentrationThe filtrate is concentrated
  4. temperaturecooled
  5. customto give further yield
  6. customThe combined product is recrystallised from alcohol-ether

Sources & evidence

ORD record
ord-8664fd5b80194feaa69737a434f63ea9
Source dataset
uspto-grants-1977_10
Patent number
US04055647

Reaction notes

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