Thionyl Chloride → HCID 118432179, compound

HRID 2207935Notes

Reaction equation

[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N:11]=[C:10]([C:20]([OH:22])=O)[CH2:9]2)=[CH:4][CH:3]=1.S(Cl)([Cl:25])=O>>[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N:11]=[C:10]([C:20]([Cl:25])=[O:22])[CH2:9]2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 118431766HCID 118431766, compound

Product 1

HCID 118432179HCID 118432179, compound

Conditions

Temperature: 100 °C

Procedure

5-(6-Bromo-pyridin-3-yl)-1-(2-chloro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid (450.0 mg, 1.2 mmol) prepared in Step 3 was added to thionyl chloride (5.0 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-(6-bromo-pyridin-3-yl)-1-(2-chloro-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-2215ea929b144621b79de376d03f2a7a
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376420B2

Reaction notes

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