Iodine → 5-(3-iodo-1H-indol-5-yl)-N-methyl-1,3,4-thiadiazol-2-amine

HRID 634152Notes

Reaction equation

HRID 634152 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[S:14][C:13]([NH:15][CH3:16])=[N:12][N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].[I:19]I.S(=O)(O)[O-].[Na+]>CN(C=O)C>[I:19][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:10]3[S:14][C:13]([NH:15][CH3:16])=[N:12][N:11]=3)[CH:5]=2)[NH:1][CH:2]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 23665763Sodium BisulfiteHCID 683279525-(1H-indol-5-yl)-N-methyl-1,3,4-thiadiazol-2-amine

Product 1

HCID 683280065-(3-iodo-1H-indol-5-yl)-N-methyl-1,3,4-thiadiazol-2-amineYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(1H-indol-5-yl)-N-methyl-1,3,4-thiadiazol-2-amine (0.5 g, 2.17 mmol) in DMF (5 mL) was added KOH (0.135 g, 2.39 mmol) followed by I2 (0.6 g, 2.39 mmol). The mixture was stirred at RT for 2 h and 10% aq sodium bisulphite (2.5 mL) solution was added. The resulting precipitate was filtered and washed with H2O, dried to give 5-(3-iodo-1H-indol-5-yl)-N-methyl-1,3,4-thiadiazol-2-amine (0.3 g, 39%). MS (ESI, pos. ion) m/z: 357 (M+1); 1HNMR (DMSO-d6, 300 MHz): δ ppm 2.9 (s, 3H), 7.7 (m, 4H), 11.8 (s, 1H).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with H2O
  3. customdried

Sources & evidence

ORD record
ord-ba9526c99c51480d82897a23b2c619fd
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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