5-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazole → HCID 58610441, compound

HRID 1594414Notes

Reaction equation

HRID 1594414 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.[Br-].[CH:10]1([Zn+])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>O1CCCC1>[CH3:8][S:7][C:4]1[N:3]=[C:2]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[S:6][N:5]=1

Participants

4

Reactant 2

HCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazoleHCID 178418970HCID 178418970, compound

Product 1

HCID 58610441HCID 58610441, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

500 mg of 5-chloro-3-methylthio-1,2,4-thiadiazole and 122 mg of {1,1′-bis(diphenylphosphino)ferrocene} dichloro palladium(II) dichloromethane complex were dissolved in 6 ml of tetrahydrofuran under nitrogen atmosphere, 6.58 ml of solution of cyclohexyl zinc bromide in tetrahydrofuran (0.5 mol/l) was added thereto under ice-cooling taking for about 5 minutes, and the reaction mixture was stirred for 16 hours at room temperature. Then, the reaction mixture was concentrated, and the residue subjected to silica gel column chromatography to give 370 mg of 3-methylthio-5-cyclohexyl-1,2,4-thiadiazole.

Workup

  1. temperatureunder ice-cooling
  2. concentrationThen, the reaction mixture was concentrated

Sources & evidence

ORD record
ord-5ba30be1a93e4dcfbf17e65ba269d784
Source dataset
uspto-grants-2007_11
Patent number
US07301032B2

Reaction notes

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