5-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazole → HCID 58610423, compound

HRID 1594416Notes

Reaction equation

HRID 1594416 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.[Br-].[CH:10]1([Zn+])[CH2:14][CH2:13][CH2:12][CH2:11]1>O1CCCC1>[CH3:8][S:7][C:4]1[N:3]=[C:2]([CH:10]2[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 178419768HCID 178419768, compound

Product 1

HCID 58610423HCID 58610423, compound

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 cyclopentyl zinc bromide in tetrahydrofuran (0.5 mol/l) was added thereto under ice-cooling taking for about 15 minutes, and the reaction mixture was stirred for 13 hours at room temperature. Then, the reaction mixture was concentrated, and the residue subjected to silica gel column chromatography to give 710 mg of 3-methylthio-5-cyclopentyl-1,2,4-thiadiazole.

Workup

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

Sources & evidence

ORD record
ord-fbf8fcca377c4581b2f969642f492dc3
Source dataset
uspto-grants-2007_11
Patent number
US07301032B2

Reaction notes

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