Sodium Chloride → HCID 23086899, compound

HRID 900840Notes

Reaction equation

HRID 900840 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+]>COCCOC>[CH3:8][S:7][C:4]1[N:3]=[C:2]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[F:9])[S:6][N:5]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazoleHCID 27343542-Fluorophenylboronic acid

Product 1

HCID 23086899HCID 23086899, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To 4 ml of 1,2-dimethoxyethane were added 284 mg of 5-chloro-3-methylthio-1,2,4-thiadiazole, 262 mg of 2-fluorophenylboronic acid, 98 mg of tetrakistriphenylphosphine palladium and 4 ml of a 2 M aqueous sodium carbonate solution, and the mixture was stirred at 80° C. for 12 hours in a nitrogen atmosphere. Then, the reaction mixture was poured into an aqueous saturated sodium chloride solution, and the mixture was extracted with t-butyl methyl ether. The residue obtained by concentration of the organic layer was subjected to silica gel column chromatography to obtain 330 mg of 3-methylthio-5-(2-fluorophenyl)-1,2,4-thiadiazole.

Workup

  1. extractionthe mixture was extracted with t-butyl methyl ether
  2. customThe residue obtained by concentration of the organic layer

Sources & evidence

ORD record
ord-8b8941be57674ef5ab70fa7e01c035be
Source dataset
uspto-grants-2008_04
Patent number
US07361675B2

Reaction notes

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