Thionyl Chloride → HCID 58180072, compound

HRID 253962Notes

Reaction equation

HRID 253962 reaction equation
C(OC([NH:6][N:7]=[C:8]([C:18]1[C:19]([Cl:25])=[N:20][CH:21]=[C:22]([Br:24])[CH:23]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=1[Cl:17])=O)C.[S:26](Cl)(Cl)=O>>[Br:24][C:22]1[CH:23]=[C:18]([C:8]2[N:7]=[N:6][S:26][C:9]=2[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=2[Cl:17])[C:19]([Cl:25])=[N:20][CH:21]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 72486478HCID 72486478, compound

Product 1

HCID 58180072HCID 58180072, compoundYield 50%

Procedure

A solution of ethyl-2-(1-(5-bromo-2-chloropyridin-3-yl)-2-(2,3-dichlorophenyl)ethylidene)hydrazinecarboxylate (3.03 mmol) was stirred in thionyl chloride (20 mL). The solution was heated from 0° C. to RT and stirred for 3.5 hours. The solvent was evaporated to give a yellow oil which was adsorbed onto Celite™ and purified by silica gel chromatography (5-40% EtOAc/hexanes) to give 5-bromo-2-chloro-3-(5-(2,3-dichlorophenyl)-1,2,3-thiadiazol-4-yl)pyridine as a yellow solid (640 mg, 50% yield over 2 steps).

Workup

  1. temperatureThe solution was heated from 0° C. to RT
  2. customThe solvent was evaporated
  3. customto give a yellow oil which
  4. custompurified by silica gel chromatography (5-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9ce9b057a4e34ac08214ceb8ad3c0e30
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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