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

HRID 634125Notes

Reaction equation

HRID 634125 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[S:12][C:13]([S:16][CH3:17])=[N:14][N:15]=3)[CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[S:20](Cl)([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>CN(C=O)C>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[S:12][C:13]([S:16][CH3:17])=[N:14][N:15]=3)[CH:9]=2)[N:4]([S:20]([C:23]2[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH:3]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 683283122-(3-iodo-1H-indol-5-yl)-5-(methylthio)-1,3,4-thiadiazole

Product 1

HCID 683288262-(3-iodo-1-tosyl-1H-indol-5-yl)-5-(methylthio)-1,3,4-thiadiazoleYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-iodo-1H-indol-5-yl)-5-(methylthio)-1,3,4-thiadiazole (7.0 g, 18.7 mmol) in DMF (70 mL) was added NaH 60% in mineral oil (1.5 g, 37.4 mmol) followed by TsCl (5.3 g, 28.1 mmol). The reaction was stirred at RT for 8 h, and the mixture was then poured into ice/H2O. The resulting precipitate was filtered, washed with water and dried to give 2-(3-iodo-1-tosyl-1H-indol-5-yl)-5-(methylthio)-1,3,4-thiadiazole (7.7 g, 78%). MS (ESI, pos. ion) m/z: 528 (M+1); 1H-NMR (DMSO-d6, 300 MHz): 2.3 (s, 3H), 2.8 (s, 3H), 7.4 (d, 2H) 7.8 (d, 1H) 7.95 (m, 3H), 8.1 (d, 1H), 8.25 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-dab1db46b99b4651a668a3c1545c3f7a
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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