Oxalyl chloride → 1-(2,6-Dimethylphenyl)-3-ethyl-2-thioxo-4,5-imidazolidinedione

HRID 720489Notes

Reaction equation

HRID 720489 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[CH3:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[NH:15][C:16]([NH:18][CH2:19][CH3:20])=[S:17]>C(Cl)Cl>[CH3:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[N:15]1[C:2](=[O:3])[C:1](=[O:5])[N:18]([CH2:19][CH3:20])[C:16]1=[S:17]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 2918886HCID 2918886, compound

Product 1

HCID 112770141-(2,6-Dimethylphenyl)-3-ethyl-2-thioxo-4,5-imidazolidinedioneYield 45.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (7.62 g; 0.06 mol) was added dropwise to the stirring solution of N-(2,6-dimethylphenyl)-N′-ethylthiourea (10.4 g; 0.05 mol) in methylene chloride (200 mL). The mixture was heated at reflux for 1 hour then evaporated to dryness. Ethanol (100 mL) was added and the mixture was heated at reflux for 1 hour then evaporated to dryness. The residue was dissolved in ethyl acetate (300 mL) and washed with 2N hydrochloric acid (500 mL) then with water (300 mL). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was crystallized from ether/hexane to give 6.0 g of 1-(2,6-Dimethylphenyl)-3-ethyl-2-thioxo-4,5-imidazolidinedione, m.p. 103–105° C. Mass spectrum; FAB (M+H)+ m/z 263. 1H-NMR (DMSO-d6; 300 MHz): δ 7.31–7.27 (m, 1H), 7.18 (d, 2H), 3.94 (q, 2H), 2.08 (s, 6H), and 1.25 ppm (t, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. customthen evaporated to dryness
  4. additionEthanol (100 mL) was added
  5. temperaturethe mixture was heated
  6. temperatureat reflux for 1 hour
  7. customthen evaporated to dryness
  8. dissolutionThe residue was dissolved in ethyl acetate (300 mL)
  9. washwashed with 2N hydrochloric acid (500 mL)
  10. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  11. customevaporated to dryness
  12. customThe residue was crystallized from ether/hexane

Sources & evidence

ORD record
ord-28a292cd63e444a089efa636171a9ee9
Source dataset
uspto-grants-2006_11
Patent number
US07135492B2

Reaction notes

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