Oxalyl chloride → HCID 73446015, compound

HRID 1268837Notes

Reaction equation

HRID 1268837 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[K+].[C:8]([C:10]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)=CC([O-])=O)#[N:9]>C(Cl)Cl>[C:8]([C:10]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)=[CH:1][C:2]([Cl:4])=[O:3])#[N:9]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 533966293-Cyano-3-(2-thienyl)acrylic acid potassium salt

Product 1

HCID 73446015HCID 73446015, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of oxalyl chloride (81.17 mL, 0.93 mol) in CH2Cl2 (350 mL) was added 3-cyano-3-thiophen-2-yl-acrylic acid potassium salt 21 (100 g, 0.45 mol) portion-wise over 20 min. An additional 250 mL of CH2Cl2 were added to assist stirring. The slurry was stirred at room temperature for 30 min and was then filtered. The potassium chloride salts were washed with copious CH2Cl2. Collected organic rinses were combined and solvent removed under vacuum to afford 84.3 g of 22, which was carried on to the next step without further purification.

Workup

  1. stirringThe slurry was stirred at room temperature for 30 min
  2. filtrationwas then filtered
  3. washThe potassium chloride salts were washed with copious CH2Cl2
  4. customsolvent removed under vacuum

Sources & evidence

ORD record
ord-6a1e7f69cb0948ac861297e01f5782f8
Source dataset
uspto-grants-2007_04
Patent number
US07199119B2

Reaction notes

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