Thionyl Chloride → HCID 118432139, compound

HRID 2208070Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[F:27])[N:19]=[C:18]([C:28]([OH:30])=O)[CH2:17]3)=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:2].S(Cl)([Cl:33])=O>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[F:27])[N:19]=[C:18]([C:28]([Cl:33])=[O:30])[CH2:17]3)=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 118431825HCID 118431825, compound

Product 1

HCID 118432139HCID 118432139, compound

Conditions

Temperature: 100 °C

Procedure

5-(3′-Ethoxy-biphenyl-4-yl)-1-(2-fluoro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid (200.0 mg, 0.49 mmol) prepared in Step 2 was added to thionyl chloride (2.0 mL). The reaction mixture was stirred at 100° C. for 2 hours and then concentrated under reduced pressure. The resulting residue was concentrated under reduced pressure three times, along with using toluene, to give 5-(3′-ethoxy-biphenyl-4-yl)-1-(2-fluoro-phenyl)-4,5-dihydro-1H-pyrazole-3-carbonyl chloride as a dark brown liquid.

Workup

concentrationconcentrated under reduced pressure
concentrationThe resulting residue was concentrated under reduced pressure three times, along with using toluene

Sources & evidence

ORD record: ord-c87a002791b9414dbb8e1a559ea71808
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376420B2

Reaction notes

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