Thionyl Chloride → HCID 89544278, compound

HRID 1050948Notes

Reaction equation

HRID 1050948 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[C:15]([CH:19]=[C:20]([CH3:22])[N:21]=3)[C:16](O)=[O:17])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:27])=O>C(Cl)Cl>[F:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[C:15]([CH:19]=[C:20]([CH3:22])[N:21]=3)[C:16]([Cl:27])=[O:17])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 89544099HCID 89544099, compound

Product 1

HCID 89544278HCID 89544278, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 50 mL round bottom flask was charged with 2-(4-(4-fluorophenoxy)phenyl)-6-methylisonicotinic acid (116 mg, 0.36 mmol) suspended in DCM and cooled in an ice bath for 20 minutes. Thionyl chloride (2 mL) was added to the suspension, which became a solution in about 10 minutes. The ice bath was removed and the reaction mixture was concentrated under reduced pressure to give 2-(4-(4-fluorophenoxy)phenyl)-6-methylisonicotinoyl chloride which was used without purification for the next reaction.

Workup

  1. temperaturecooled in an ice bath for 20 minutes
  2. customin about 10 minutes
  3. customThe ice bath was removed
  4. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-71ee76cb2ac549b28b4a9de6519fa1d4
Source dataset
uspto-grants-2016_07
Patent number
US09388137B2

Reaction notes

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