Indole → HCID 12934735, compound

HRID 1075804Notes

Reaction equation

HRID 1075804 reaction equation
[I:1]I.[I-].[K+].[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6]1.[NH:14]1[CH2:20][CH2:19][CH2:18][CH2:17][N:16]=[C:15]1[SH:21]>O.CO>[IH:1].[NH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][N:14]=[C:15]1[S:21][C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:5][CH:6]=1

Participants

7

Reactant 4

HCID 798IndoleHCID 807IodineHCID 4875Potassium IodideHCID 178527863HCID 178527863, compound

Product 1

HCID 12934735HCID 12934735, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 12.7 g of iodine and 20 g of potassium iodide in 100 ml of water is added dropwise to a well-stirred mixture of 5.85 g of indole in 20 ml methanol and 6.5 g of 4,5,6,7-tetrahydro-1H-1,3-diazepine-2-thiol in 100 ml methanol. The reaction mixture is stirred at room temperature for 2 hours. The crystalline precipitate formed was filtered off and recrystallized from a mixture of methanol, ethyl acetate and ether to afford 3-(4,5,6,7-tetrahydro-1H-1,3-diazepin-2-ylthio)-indole hydriodide which melts at 236° (with decomposition).

Workup

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

Sources & evidence

ORD record
ord-3ccdc3d6ea224afda3a25f9a3c84eba9
Source dataset
uspto-grants-1976_05
Patent number
US03954757

Reaction notes

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