5-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazole → 3-Methylthio-5-(cyclohexyl)methyl-1,2,4-thiadiazole

HRID 1594418Notes

Reaction equation

HRID 1594418 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.[Br-].[CH:10]1([CH2:16][Zn+])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>O1CCCC1>[CH3:8][S:7][C:4]1[N:3]=[C:2]([CH2:16][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 178419774HCID 178419774, compound

Product 1

HCID 586104393-Methylthio-5-(cyclohexyl)methyl-1,2,4-thiadiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.00 g of 5-chloro-3-methylthio-1,2,4-thiadiazole and 244 mg of {1,1′-bis(diphenylphosphino)ferrocene} dichloro palladium(II) dichloromethane complex were dissolved in 12 ml of tetrahydrofuran under nitrogen atmosphere, 13.2 ml of solution of (cyclohexyl)methyl zinc bromide in tetrahydrofuran (0.5 mol/l) was added thereto under ice-cooling taking for about 10 minutes, and the reaction mixture was stirred for 30 minutes under ice-cooling and for 8 hours at room temperature. Then, the reaction mixture was concentrated, and the residue subjected to silica gel column chromatography to give 1.29 g of 3-methylthio-5-(cyclohexyl)methyl-1,2,4-thiadiazole.

Workup

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

Sources & evidence

ORD record
ord-b796f171d80c4d67b12595abc8432752
Source dataset
uspto-grants-2007_11
Patent number
US07301032B2

Reaction notes

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