Indole → 3-(1-Methyl-2-imidazolin-2-ylthio)-indole hydriodide

HRID 973233Notes

Reaction equation

HRID 973233 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:10][N:11]1[CH2:15][CH2:14][NH:13][C:12]1=[S:16].[I:17]I.[I-].[K+]>CO.O>[IH:17].[CH3:10][N:11]1[CH2:15][CH2:14][N:13]=[C:12]1[S:16][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

7

Reactant 4

HCID 798IndoleHCID 807IodineHCID 4875Potassium IodideHCID 2733224Methylethylenethiourea

Product 1

HCID 129347043-(1-Methyl-2-imidazolin-2-ylthio)-indole hydriodide

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 5.85 g indole in 50 ml methanol and 5.8 g 1-methyl-2-imidazolidinethione in 100 ml methanol is treated with a solution of 12.7 g of iodine and 25 g potassium iodide in 100 ml water. The mixture is stirred for 2 hours at room temperature, the clear solution is concentrated in vacuo to one third of the original volume and cooled. The solid which separates is filtered off and recrystallized from a mixture of methanol and ethyl acetate to give 3-(1-methyl-2-imidazolin-2-ylthio)-indole hydriodide melting at 215°-216°.

Workup

  1. concentrationthe clear solution is concentrated in vacuo to one third of the original volume
  2. temperaturecooled
  3. filtrationThe solid which separates is filtered off
  4. customrecrystallized from a mixture of methanol and ethyl acetate

Sources & evidence

ORD record
ord-1533f33cd95240e58fbf2f9b4e5a4434
Source dataset
uspto-grants-1977_10
Patent number
US04055647

Reaction notes

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