Thionyl Chloride → HCID 58575562, compound

HRID 1807835Notes

Reaction equation

HRID 1807835 reaction equation
[Cl:1][C:2]1[C:3]([NH:16][NH:17][C:18]([CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=O)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.S(Cl)(Cl)=O>C(#N)C>[Cl:1][C:2]1[C:3]2[N:4]([C:18]([CH:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[N:17][N:16]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58575049HCID 58575049, compound

Product 1

HCID 58575562HCID 58575562, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 1.20 g of methyl 3-chloro-2-[2-(tetrahydro-2H-pyran-4-ylcarbonyl)hydrazino]quinoxaline-6-carboxylate and 36 mL of acetonitrile was added 0.5 mL of thionyl chloride, followed by stirring at 90° C. for 4.5 hours. The solvent was evaporated under reduced pressure, to the obtained residue was added water, and the solid was collected by filtration and dried under reduced pressure to obtain 1.13 g of methyl 4-chloro-1-(tetrahydro-2H-pyran-4-yl)[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylate.

Workup

  1. customThe solvent was evaporated under reduced pressure, to the obtained residue
  2. additionwas added water
  3. filtrationthe solid was collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-e14656389bdb40df972489969aae607a
Source dataset
uspto-grants-2013_01
Patent number
US08357688B2

Reaction notes

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