Iodine → HCID 12934741, compound

HRID 973239Notes

Reaction equation

HRID 973239 reaction equation
[I:1]I.[I-].[K+].[Br:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2.[NH:15]1[CH2:21][CH2:20][CH2:19][CH2:18][NH:17][C:16]1=[S:22]>O.CO>[IH:1].[Br:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[S:22][C:16]1[NH:17][CH2:18][CH2:19][CH2:20][CH2:21][N:15]=1

Participants

7

Reactant 4

HCID 807IodineHCID 4875Potassium IodideHCID 249055-BromoindoleHCID 7365891,3-Diazepane-2-thione

Product 1

HCID 12934741HCID 12934741, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 6.35 g of iodine and 11 g of potassium iodide in 50 ml of water is added dropwise to a mixture of 4.9 g of 5-bromoindole in 35 ml methanol and 3.25 g of 4,5,6,7-tetrahydro-1H-1,3-diazepine-2-thione in 50 ml of methanol. The reaction mixture is allowed to be stirred at room temperature for 2 hours. The crystalline precipitate formed is filtered off and recrystallized from a mixture of methanol and ethyl acetate to yield 5-bromo-3-(4,5,6,7-tetrahydro-1H-1,3-diazepin-2-ylthio)indole hydriodide which melts at 243°-246° (with decomposition).

Workup

  1. customThe crystalline precipitate formed
  2. filtrationis filtered off
  3. customrecrystallized from a mixture of methanol and ethyl acetate

Sources & evidence

ORD record
ord-73625f33ebba4c7189f306d0ef396daf
Source dataset
uspto-grants-1977_10
Patent number
US04055647

Reaction notes

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