Indole → HCID 12934747, compound

HRID 973226Notes

Reaction equation

HRID 973226 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.[SH:14][C:15]1[NH:16][CH2:17][CH:18]([OH:21])[CH2:19][N:20]=1>CO.O>[IH:10].[OH:21][CH:18]1[CH2:19][NH:20][C:15]([S:14][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)=[N:16][CH2:17]1

Participants

7

Reactant 4

HCID 798IndoleHCID 807IodineHCID 4875Potassium IodideHCID 178516796HCID 178516796, compound

Product 1

HCID 12934747HCID 12934747, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 9.36 g of indole in 60 ml methanol is added dropwise to a well-stirred solution of 40 g potassium iodide and 20.3 g of iodine in 120 ml of water at room temperature. This is reacted with a solution of 10.6 g of 2-mercapto-1,4,5,6-tetrahydro-5-pyrimidinol in 1800 ml of 50% aqueous methanol. The reaction mixture is stirred at room temperature for 2 hours and worked up in the manner, described under Example 1 to yield 3-(5-hydroxy-1,4,5,6-tetrahydro-2-pyrimidinylthio)-indole hydriodide which melts at 228°-229° (with decomposition) after recrystallization from a mixture of methanol, ethyl acetate and ether.

Sources & evidence

ORD record
ord-44050cab12a24a8dbc1dd1406618369a
Source dataset
uspto-grants-1977_10
Patent number
US04055647

Reaction notes

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