Oxalyl chloride → HCID 86668989, compound

HRID 2366170Notes

Reaction equation

HRID 2366170 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl: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]([Cl: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 66801889HCID 66801889, compound

Product 1

HCID 86668989HCID 86668989, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of (E)-3-(2-(2,6-dichlorophenyl)thiazol-4-yl)acrylic acid (5.7 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 for 2 hours at room temperature and then concentrated under reduced pressure to give the crude desired product (6.0 g, 99% yield), which was used in the next step without purification.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3810bf36f1bf47d9802cfe4c9eb6da15
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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