Oxalyl chloride → HCID 10192975, compound

HRID 720485Notes

Reaction equation

HRID 720485 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH:17][CH2:18][CH3:19])=[S:16])=[C:10]([CH3:20])[CH:9]=1>C(Cl)Cl>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:2](=[O:3])[C:1](=[O:5])[N:17]([CH2:18][CH3:19])[C:15]2=[S:16])=[C:10]([CH3:20])[CH:9]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 976537HCID 976537, compound

Product 1

HCID 10192975HCID 10192975, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (10.5 g; 0.082 mol) was added dropwise to the stirring solution of N-(4-chloro-2-methylphenyl)-N′-ethylthiourea (17 g; 0.075 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 (500 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 ethyl acetate/hexane to give 13.2 g of 1-(4-chloro-2-methylphenyl)-3-ethyl-2-thioxo-4,5-imidazolidinedione, m.p. 161–162° C. Mass spectrum; FAB (M+H)+ m/z 283. 1H-NMR (DMSO-d6; 300 MHz): δ 7.49 (d, 1H), 7.39 (m,1H), 7.33 (d, 1H), 3.91 (m, 2H), 2.16 (s, 3H), and 1.23 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 (500 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 ethyl acetate/hexane

Sources & evidence

ORD record
ord-fd00f7a3313943298338b55054ee9b4a
Source dataset
uspto-grants-2006_11
Patent number
US07135492B2

Reaction notes

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