Indole → HCID 12934721, compound

HRID 1075792Notes

Reaction equation

HRID 1075792 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[I-:10].[K+].II.[CH3:14][N:15]1[CH2:20][CH2:19][CH2:18][N:17]=[C:16]1[SH:21]>CO.O>[IH:10].[CH3:14][N:15]1[CH2:20][CH2:19][CH2:18][N:17]=[C:16]1[S:21][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 178480417HCID 178480417, compound

Product 1

HCID 12934721HCID 12934721, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 11.7 g of indole in 100 ml of methanol is added portionwise to a stirred solution of 50 g potassium iodide and 25.4 g of iodine in 150 ml of water at room temperature. This mixture is further treated with a solution of 13 g of 1-methyl-1,4,5,6-tetrahydro-2-pyrimidinethiol in 150 ml of methanol. The reaction mixture is then stirred at room temperature for 2 hours, filtered and the filtrate concentrated to one-fourth of the original volume and cooled. A crystalline precipitate is formed. This is filtered and recrystallised from a mixture of methanol, ethyl acetate and ether to yield 3-(1-methyl-1,4,5,6-tetrahydro-2-pyrimidinylthio)-indole hydriodide which melts at 207°.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated to one-fourth of the original volume
  3. temperaturecooled
  4. customA crystalline precipitate is formed
  5. filtrationThis is filtered
  6. customrecrystallised from a mixture of methanol, ethyl acetate and ether

Sources & evidence

ORD record
ord-e13dd7ac27834fe392cb006f94133169
Source dataset
uspto-grants-1976_05
Patent number
US03954757

Reaction notes

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