Indole → HCID 86733374, compound

HRID 973220Notes

Reaction equation

HRID 973220 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[NH:10]1[CH2:15][CH2:14][CH2:13][N:12]=[C:11]1[SH:16].[I:17]I.[I-].[K+]>CO.O>[IH:17].[NH:12]1[CH2:13][CH2:14][CH2:15][N:10]=[C:11]1[S:16][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 178527864HCID 178527864, compound

Product 1

HCID 86733374HCID 86733374, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 11.7 g indole in 50 ml methanol and 11.6 g 1,4,5,6-tetrahydro-2- pyrimidinethiol in 100 ml methanol is added to a well-stirred solution of 25.4 g iodine and 50 g potassium iodide in 100 ml water. The mixture is stirred for 12 hours at room temperature and cooled. The crystalline product is filtered off. The filtrate is concentrated to one third of the original volume, and cooled to yield more of the resulting product. The combined product is recrystallised from alcohol to give 3-(1,4,5,6-tetrahydro-2-pyrimidinylthio)-indole hydriodide, melting at 251°.

Workup

  1. temperaturecooled
  2. filtrationThe crystalline product is filtered off
  3. concentrationThe filtrate is concentrated to one third of the original volume
  4. temperaturecooled
  5. customto yield more of the resulting product
  6. customThe combined product is recrystallised from alcohol

Sources & evidence

ORD record
ord-515c1e1bd0d145f6bb8877e1cc1fdfec
Source dataset
uspto-grants-1977_10
Patent number
US04055647

Reaction notes

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