Oxalyl chloride → HCID 10192786, compound

HRID 720483Notes

Reaction equation

HRID 720483 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][CH3:19])=[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]([CH3:19])[C:16]1=[S:17]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 686503HCID 686503, compound

Product 1

HCID 10192786HCID 10192786, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (8.4 g; 0.066 mol) was added dropwise to the stirring solution of N-(2,6-dimethyl phenyl)-N′-methylthiourea (6.4 g; 0.033 mol) in methylene chloride (100 mL). The mixture was heated at reflux for 2 hours then evaporated to dryness. Ethanol (100 mL) was added and the mixture was heated at reflux for 1 hour. The solvent was concentrated. The precipitated solid was collected by filtration and dried to give 5.4 g of 1-(2,6-Dimethylphenyl)-3-methyl-2-thioxo-4,5-imidazolidinedione, m.p. 144–146° C. Mass spectrum; (El, M.+) m/z248. 1H-NMR (DMSO-d6; 300 MHz): δ 7.30 (t, 1H), 7.18 (d, 2H), 3.33 (s, 3H), and 2.08 ppm (s, 6H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customthen evaporated to dryness
  4. additionEthanol (100 mL) was added
  5. temperaturethe mixture was heated
  6. temperatureat reflux for 1 hour
  7. concentrationThe solvent was concentrated
  8. filtrationThe precipitated solid was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-740c101ae38447508703ca563fda393e
Source dataset
uspto-grants-2006_11
Patent number
US07135492B2

Reaction notes

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