Iodine → HCID 12934723, compound

HRID 973228Notes

Reaction equation

HRID 973228 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([OH:14])=[O:13])=[CH:6]2.[I-:15].[K+].II.[NH:19]1[CH2:24][CH2:23][CH2:22][N:21]=[C:20]1[SH:25]>CO.O>[IH:15].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([OH:14])=[O:13])=[C:6]2[S:25][C:20]1[NH:21][CH2:22][CH2:23][CH2:24][N:19]=1

Participants

7

Reactant 4

HCID 807IodineHCID 4875Potassium IodideHCID 204015-Methoxyindole-2-carboxylic acidHCID 178527864HCID 178527864, compound

Product 1

HCID 12934723HCID 12934723, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 5.7 g of 5-methoxy-indole-2-carboxylic acid in 70 ml of hot methanol is added portionwise to a solution of 15 g potassium iodide and 7.6 g of iodine in 45 ml of water. This is further treated with a solution of 3.48 g of 1,4,5,6-tetrahydro-2-pyrimidinethiol in 70 ml of hot methanol, stirred at room temperature for 2 hours and filtered. The filtrate is worked up in the manner described under Example 1 to yield 5-methoxy-3-(1,4,5,6-tetrahydro-2-pyrimidinylthio)-indole-2-carboxylic acid hydriodide which melts at 239°-240° after recrystallization from a mixture of methanol, ethyl acetate and ether.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-079b3b61a2574f67800e36ef5ad96cb0
Source dataset
uspto-grants-1977_10
Patent number
US04055647

Reaction notes

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