Iodine → 5-Bromo-3-(1,4,5,6-tetrahydro-2-pyrimidinylthio)-indole hydriodide

HRID 973224Notes

Reaction equation

HRID 973224 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[I].[K].[I:13]I.[NH:15]1[CH2:20][CH2:19][CH2:18][N:17]=[C:16]1[SH:21]>CO.O>[IH:13].[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[S:21][C:16]1[NH:17][CH2:18][CH2:19][CH2:20][N:15]=1

Participants

7

Reactant 4

HCID 807IodineHCID 249055-BromoindoleHCID 178506587HCID 178506587, compoundHCID 178527864HCID 178527864, compound

Product 1

HCID 129347175-Bromo-3-(1,4,5,6-tetrahydro-2-pyrimidinylthio)-indole hydriodide

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 19.6 g of 5-bromo-indole in 50 ml of methanol is added to a stirred solution of 50 g potassium iodine and 25.4 g of iodine in 150 ml of water at room temperature. The mixture is further treated with a solution of 11.6 g of 1,4,5,6-tetrahydro-2-pyrimidinethiol in 270 ml of warm methanol. The reaction mixture is then stirred at room temperature for 2 hours, filtered and the filtrate is concentrated to one-fifth of the original volume and cooled. A crystalline precipitate is formed. This is filtered and recrystallised from a mixture of methanol, ethylacetate and ether to yield 5-bromo-3-(1,4,5,6-tetrahydro-2-pyrimidinylthio)-indole hydriodide which melts at 241°-242°.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate is concentrated to one-fifth of the original volume
  3. temperaturecooled
  4. customA crystalline precipitate is formed
  5. filtrationThis is filtered
  6. customrecrystallised from a mixture of methanol, ethylacetate and ether

Sources & evidence

ORD record
ord-26d99a0f6db545dcb393be914748cfac
Source dataset
uspto-grants-1977_10
Patent number
US04055647

Reaction notes

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