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

HRID 634250Notes

Reaction equation

HRID 634250 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[S:14][N:13]=[C:12]([NH:15][CH2:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)[N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].[I:27]I.S(=O)(O)[O-].[Na+]>CN(C=O)C>[I:27][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:10]3[S:14][N:13]=[C:12]([NH:15][CH2:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)[N:11]=3)[CH:5]=2)[NH:1][CH:2]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 23665763Sodium BisulfiteHCID 683283425-(1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine

Product 1

HCID 683285295-(3-iodo-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amineYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine (0.67 g, 1.99 mmol) in DMF (7 mL) was added KOH pellets (0.325 g, 5.95 mmol) followed by I2 (1 g, 3.98 mmol) in portions at 0° C. The reaction was stirred for 1 h at RT. 10% aq sodium bisulphite solution was added to the mixture and solid precipitate was obtained. The suspension was filtered and washed with H2O (2×20 mL) and dried under vacuum to give 5-(3-iodo-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine (800 mg, 87%) as an off brown solid. MS (ESI, pos. ion) m/z: 463.0 (M+1); 1H-NMR (300 MHz, CDCl3): δ 8.72 (brs, 1H), 8.02 (d, J=6 Hz, 1H), 7.77 (d, J=8.4 Hz, 1H), 7.43 (d, J=8.7 Hz, 1H), 7.36-7.33 (m, 2H), 6.90 (d, J=8.4 Hz, 1H), 5.43 (m, 1H), 4.63 (d, J=5.7 Hz, 2H), 3.80 (s, 3H).

Workup

  1. customsolid precipitate was obtained
  2. filtrationThe suspension was filtered
  3. washwashed with H2O (2×20 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-13a8d19f6f294bcbae45179d25ff74da
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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