3,4-Dichloro-1,2,5-thiadiazole → 3-Chloro-4-phenyl-1,2,5-thiadiazole

HRID 1167985

Reaction equation

HRID 1167985 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)CCC.[Cl:20][C:21]1[C:25](Cl)=[N:24][S:23][N:22]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:20][C:21]1[C:25]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[N:24][S:23][N:22]=1

Participants

5

Reactant 2

HCID 798043,4-Dichloro-1,2,5-thiadiazoleHCID 607632Tributylphenyltin

Product 1

HCID 27640443-Chloro-4-phenyl-1,2,5-thiadiazoleYield 48%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

1.9 g (0.00517 mol) of tributylphenyl stannane and 0.29 g (0.00025 mol) of tetrakis (triphenylphosphine)palladium(0) were added to a solution of 0.775 g (0.005 mol) of 3,4-dichloro-1,2,5-thiadiazole in 10 mL of toluene under nitrogen and heated at reflux. After 8 h, 0.145 g (1.25×10−4 mol) of tetrakis(triphenylphosphine)palladium(0) were added. After 24 h of reflux, 48% of product formed by quantitative HPLC (versus a reference prepared as reported by L. Weinstock et al., J. Org. Chem., vol. 32, p 2823 (1967)).

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. temperatureAfter 24 h of reflux

Sources & evidence

ORD record
ord-83c8cb054e6a45febf5ec5ba39f719a3
Source dataset
uspto-grants-2003_09
Patent number
US06620940B1

Linked notes

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