1,2-Dimethoxyethane → HCID 23086909, compound

HRID 900841Notes

Reaction equation

HRID 900841 reaction equation
COCCOC.Cl[C:8]1[S:12][N:11]=[C:10]([S:13][CH3:14])[N:9]=1.[Cl:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:14][S:13][C:10]1[N:9]=[C:8]([C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:15])[S:12][N:11]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazoleHCID 2734323(3-Chlorophenyl)boronic acid

Product 1

HCID 23086909HCID 23086909, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 25 ml of 1,2-dimethoxyethane were added 2.0 g of 5-chloro-3-methylthio-1,2,4-thiadiazole, 2.25 g of 3-chlorophenylboronic acid, 694 mg of tetrakistriphenylphosphine palladium and about 25 ml of a 2 M aqueous sodium carbonate solution, and the mixture was heated under reflux for 3 hours in a nitrogen atmosphere. Then, the reaction mixture was poured into water, and the mixture was extracted with t-butyl methyl ether. The organic layer was dried with anhydrous sodium sulfate, and the residue obtained by concentration was subjected to silica gel column chromatography to obtain 1.48 g of 3-methylthio-5-(2-chlorophenyl)-1,2,4-thiadiazole.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours in a nitrogen atmosphere
  3. extractionthe mixture was extracted with t-butyl methyl ether
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. customthe residue obtained by concentration

Sources & evidence

ORD record
ord-66779be1bd4541e4bbf7f288773efee7
Source dataset
uspto-grants-2008_04
Patent number
US07361675B2

Reaction notes

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