Oxalyl chloride → HCID 86723301, compound

HRID 2366191Notes

Reaction equation

HRID 2366191 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[S:10][CH:11]=[C:12](/[CH:14]=[CH:15]/[C:16]([OH:18])=O)[N:13]=1.C(Cl)(=O)C([Cl:22])=O>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[S:10][CH:11]=[C:12](/[CH:14]=[CH:15]/[C:16]([Cl:22])=[O:18])[N:13]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 68155901HCID 68155901, compound

Product 1

HCID 86723301HCID 86723301, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of (E)-3-(2-(2-chloro-6-fluorophenyl)thiazol-4-yl)acrylic acid (5.4 g, 19 mmol) in DCM (20 mL) was added oxalyl chloride (4.8 g, 38 mmol) and 2 drops of DMF. The resulting mixture was stirred at room temperature for 2 hours and then concentrated under reduced pressure to give the crude product (5.7 g, 100% yield), which was used in the next step without purification.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92bf96003e264cfaa6793d003ad9091c
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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