Ethoxalyl chloride → HCID 10286073, compound

HRID 720482Notes

Reaction equation

HRID 720482 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5]CC)=O.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:21])=[C:14]([NH:16][C:17]([NH:19][CH3:20])=[S:18])[CH:15]=1>C(Cl)(Cl)Cl>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:21])=[C:14]([N:16]2[C:2](=[O:8])[C:3](=[O:5])[N:19]([CH3:20])[C:17]2=[S:18])[CH:15]=1

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 2252731HCID 2252731, compound

Product 1

HCID 10286073HCID 10286073, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethyl chlorooxoacetate (16.3 g; 0.128 mol) was added dropwise to the solution N-(5-chloro-2-methylphenyl)-N′-methylthiourea (10.7 g; 0.05 mol) in chloroform (200 mL). The mixture was heated at reflux for 4 hours then evaporated to dryness. The residue was treated with ether (200 mL). The precipitated solid was collected by filtration and dried to give 9.7 g of 1-(5-chloro-2-methylphenyl)-3-methyl-2-thioxo-4,5-imidazolidinedione, m.p. 171–173° C. Mass spectrum; (El, M.+) m/z268/270. 1H-NMR (DMSO-d6; 300 MHz): δ 7.50–7.47 (m, 1H), 7.42–7.40 (m, 2H), 3.31 (s, 3H), and 2.15 ppm (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 hours
  3. customthen evaporated to dryness
  4. additionThe residue was treated with ether (200 mL)
  5. filtrationThe precipitated solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-f0f25e0970ae42418162544aa8fa74a8
Source dataset
uspto-grants-2006_11
Patent number
US07135492B2

Reaction notes

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