Iodine → 2-(3-iodo-1H-indol-5-yl)-5-(methylthio)-1,3,4-thiadiazole

HRID 634121Notes

Reaction equation

HRID 634121 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[S:11][C:12]([S:15][CH3:16])=[N:13][N:14]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].[I:19]I>CN(C=O)C>[I:19][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:10]3[S:11][C:12]([S:15][CH3:16])=[N:13][N:14]=3)[CH:5]=2)[NH:1][CH:2]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 68328215HCID 68328215, compound

Product 1

HCID 683283122-(3-iodo-1H-indol-5-yl)-5-(methylthio)-1,3,4-thiadiazoleYield 75.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(1H-indol-5-yl)-5-(methylthio)-1,3,4-thiadiazole (18.5 g, 74.8 mmol) in DMF (190 mL) was added KOH (16.2 g, 299 mmol) followed by I2 (38 g, 149.7 mmol). The reaction was stirred at RT for 2 h, and was quenched with 10% aq sodium bisulphate solution. The resulting precipitate was filtered and washed with H2O to give 2-(3-iodo-1H-indol-5-yl)-5-(methylthio)-1,3,4-thiadiazole (21 g, 75%). MS (ESI, pos. ion) m/z: 373.8 (M+1). 1HNMR (DMSO-d6, 300 MHz): 2.8 (s, 3H), 7.5 (d, 1H), 7.7 (m, 2H), 12.0 (s, 1H).

Workup

  1. customwas quenched with 10% aq sodium bisulphate solution
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with H2O

Sources & evidence

ORD record
ord-8ebd26ce063e426a90eaf61199b0a3ee
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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