Iodine → HCID 12934727, compound

HRID 1075794Notes

Reaction equation

HRID 1075794 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].[I-:13].[K+].II.[CH3:17][N:18]1[CH2:23][CH2:22][CH2:21][N:20]=[C:19]1[SH:24]>CO.O>[IH:13].[CH3:17][N:18]1[CH2:23][CH2:22][CH2:21][N:20]=[C:19]1[S:24][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 178480417HCID 178480417, compound

Product 1

HCID 12934727HCID 12934727, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 28.98 g of indole-2-carboxylic acid in 300 ml of methanol is added to a well-stirred solution of 90 g of potassium iodide and 45.6 g of iodine in 270 ml of water at room temperature. This mixture is further treated with a solution of 23.4 g of 1-methyl-1,4,5,6-tetrahydro-2-pyrimidinethiol in 420 ml of warm methanol. The reaction mixture is stirred for 2 hours at room temperature and worked up in the manner described unter Example 1 to yield 3-(1-methyl-1,4,5,6-tetrahydro-2-pyrimidinylthio)-indole-2-carboxylic acid hydriodide which melts at 230°-231° after recrystallization from a mixture of methanol, ethyl acetate and ether.

Sources & evidence

ORD record
ord-e08a3fb94b454409b2c6a5dd11c892d9
Source dataset
uspto-grants-1976_05
Patent number
US03954757

Reaction notes

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