Methanol → HCID 21833780, compound

HRID 1741072Notes

Reaction equation

S(Cl)(Cl)=O.[CH3:5][C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[N:16][CH:15]=[CH:14][N:13]=2)[CH:9]=[CH:8][C:7]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24]([OH:26])=[O:25])=[CH:20][CH:19]=1.[CH3:27]O>>[CH3:5][C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[N:16][CH:15]=[CH:14][N:13]=2)[CH:9]=[CH:8][C:7]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=1

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 218337412'-Methyl-4'-pyrazinylbiphenyl-4-carboxylic acid

Product 1

HCID 21833780HCID 21833780, compoundYield 65%

Procedure

Thionyl chloride (0.076 ml, 1.043 mmol) was added to methanol (7 ml) at 0° C. After 15 minutes, 2'-methyl-4'-pyrazinylbiphenyl-4-carboxylic acid (D85, 0.216 g, 0.745 mmol) was added and the mixture was heated to reflux. After 5 h, the reaction mixture was allowed to cool and was left at room temperature overnight. The reaction mixture was then evaporated under reduced pressure and the residue was partitioned between dichloromethane (25 ml) and 10% sodium carbonate solution (20 ml). The aqueous layer was then extracted with dichloromethane (1×10 ml), and the combined organic layers were then dried (Na2SO4) and evaporated under reduced pressure to give the title compound as a yellow/brown solid (0.146 g, 65%).

Workup

temperaturethe mixture was heated to reflux
waitAfter 5 h
temperatureto cool
waitwas left at room temperature overnight
customThe reaction mixture was then evaporated under reduced pressure
customthe residue was partitioned between dichloromethane (25 ml) and 10% sodium carbonate solution (20 ml)
extractionThe aqueous layer was then extracted with dichloromethane (1×10 ml)
dry with materialthe combined organic layers were then dried (Na2SO4)
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-1dbaeec8010f4576a49c66f05d76fce8
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05972951

Reaction notes

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