Ethoxalyl chloride → 1-(5-Chloro-2-methylphenyl)-3-ethyl-2-thioxo-4,5-imidazolidinedione

HRID 720479Notes

Reaction equation

HRID 720479 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5]CC)=O.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:22])=[C:14]([NH:16][C:17]([NH:19][CH2:20][CH3:21])=[S:18])[CH:15]=1>C(Cl)(Cl)Cl>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:22])=[C:14]([N:16]2[C:2](=[O:8])[C:3](=[O:5])[N:19]([CH2:20][CH3:21])[C:17]2=[S:18])[CH:15]=1

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 4937761N-(5-chloro-2-methylphenyl)-N'-ethylthiourea

Product 1

HCID 113580321-(5-Chloro-2-methylphenyl)-3-ethyl-2-thioxo-4,5-imidazolidinedioneYield 83.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethyl chlorooxoacetate (12.3 g; 0.09 mol) was added dropwise to the solution N-(5-chloro-2-methylphenyl)-N′-ethylthiourea (13.7 g; 0.06 mol) in chloroform (300 mL). The mixture was heated at reflux for 3 hour then evaporated to dryness. The residue was dissolved in ethyl acetate (400 mL) and washed with saturated sodium bicarbonate solution (300 mL), then with water (300 mL). ). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. The residual solid was slurried in ether and filtered. The solid was washed with ether and air dried to give 1-(5-Chloro-2-methylphenyl)-3-ethyl-2-thioxo-4,5-imidazolidinedione (14.1 g), m.p. 173–174° C. Mass spectrum; (El, M.+) m/z 382/384. 1 H-NMR (DMSO-d6; 300 MHz): δ 7.49–7.40 (m, 3H), 3.92 (m, 2H), 2.15 (s, 3H), and 1.23 ppm (t, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hour
  3. customthen evaporated to dryness
  4. dissolutionThe residue was dissolved in ethyl acetate (400 mL)
  5. washwashed with saturated sodium bicarbonate solution (300 mL)
  6. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  7. customevaporated to dryness
  8. filtrationfiltered
  9. washThe solid was washed with ether and air
  10. customdried

Sources & evidence

ORD record
ord-e4ca419dd77c47b89233cbf7f00830ff
Source dataset
uspto-grants-2006_11
Patent number
US07135492B2

Reaction notes

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