Thionyl Chloride → HCID 58828522, compound

HRID 2358302Notes

Reaction equation

HRID 2358302 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([C:6]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:7]=1[C:8](O)=[O:9])=[O:5].S(Cl)([Cl:23])=O>ClCCl.CN(C=O)C>[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([C:6]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:7]=1[C:8]([Cl:23])=[O:9])=[O:5]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 58828528HCID 58828528, compound

Product 1

HCID 58828522HCID 58828522, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-2-fluorobenzoyl)-4-methoxybenzoic acid (84) (2.05 g, 7.48 mmol) in 50 mL of dichloromethane was added thionyl chloride (2.40 mL, 14.9 mmol), followed by 3 drops of DMF. The reaction was warmed to reflux. After 1 hour, LC-MS (aliquot quenched with pyrrolidine/ACN/H2O) showed that the reaction was complete (ESI+MS for corresponding pyrrolidine amide: 328.2 [M+H]+). The reaction was concentrated in vacuo to provide an oil which was used in the next step without further purification.

Workup

  1. temperatureThe reaction was warmed to reflux
  2. customLC-MS (aliquot quenched with pyrrolidine/ACN/H2O)
  3. concentrationThe reaction was concentrated in vacuo
  4. customto provide an oil which
  5. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-c56042b7fb9945ea811d5765ca9152ca
Source dataset
uspto-grants-2010_07
Patent number
US07763614B2

Reaction notes

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