Thionyl Chloride → HCID 87393347, compound

HRID 2219417Notes

Reaction equation

HRID 2219417 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13](O)=[O:14])=[C:11]([CH2:16][O:17][CH3:18])[O:10][N:9]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:21])=O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([Cl:21])=[O:14])=[C:11]([CH2:16][O:17][CH3:18])[O:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57457706HCID 57457706, compound

Product 1

HCID 87393347HCID 87393347, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
60 °C

Procedure

To a suspension of 3-(4-fluoro-phenyl)-5-methoxymethyl-isoxazole-4-carboxylic acid (2.51 g, 10.0 mmol) in thionyl chloride (4.0 mL) was added two drops of DMF, and the resulting reaction mixture was heated at 60° C. for 3 h. After cooling to room temperature, the mixture was concentrated under reduced pressure to afford the crude title compound (2.7 g, 100%) which was obtained as a light yellow liquid and used directly in the next step without further purification.

Workup

  1. customthe resulting reaction mixture
  2. temperatureAfter cooling to room temperature
  3. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a9ec97fac5e5479aaee5248dc5973f08
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

Loading…