Oxalyl chloride → HCID 73446015, compound

HRID 1868290Notes

Reaction equation

HRID 1868290 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-2f8534574f344b848fdc6f33cbfe4136
Source dataset
uspto-grants-2009_12
Patent number
US07635695B2

Reaction notes

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