Iodine → HCID 12934715, compound

HRID 973222Notes

Reaction equation

HRID 973222 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].[NH:13]1[CH2:18][CH2:17][CH2:16][N:15]=[C:14]1[SH:19].[I:20]I.[I-].[K+]>CO.O>[IH:20].[NH:15]1[CH2:16][CH2:17][CH2:18][N:13]=[C:14]1[S:19][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 178527864HCID 178527864, compound

Product 1

HCID 12934715HCID 12934715, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 6.4 g indole-2-carboxylic acid in 25 ml methanol and 4.6 g 1,4,5,6-tetrahydro-2-pyrimidinethiol in 50 ml methanol is added to a well-stirred solution of 10.1 g iodine and 16.3 g potassium iodide in 50 ml water. The mixture is stirred at room temperature for 11/2 hours, and cooled. The crystalline product is filtered off. A second yield is obtained by concentrating the filtrate to a small volume and cooling. The combined product is recrystallised from hot water to give 3-(1,4,5,6-tetrahydro-2-pyrimidinylthio)-indole-2-carboxylic acid hydriodide melting at 252°.

Workup

  1. temperaturecooled
  2. filtrationThe crystalline product is filtered off
  3. customA second yield
  4. customis obtained
  5. concentrationby concentrating the filtrate to a small volume
  6. temperaturecooling
  7. customThe combined product is recrystallised from hot water

Sources & evidence

ORD record
ord-1bf5e901099d4228b7a5c0c62d793a66
Source dataset
uspto-grants-1977_10
Patent number
US04055647

Reaction notes

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