Oxalyl chloride → HCID 11161080, compound

HRID 720484Notes

Reaction equation

HRID 720484 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[CH2:7]([NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)=[S:11])[CH3:8]>C(Cl)Cl>[CH2:7]([N:9]1[C:2](=[O:3])[C:1](=[O:5])[N:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:10]1=[S:11])[CH3:8]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 6983421-ethyl-3-(4-fluorophenyl)thiourea

Product 1

HCID 11161080HCID 11161080, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (12.7 g; 0.1 mol) was added dropwise to the stirring solution of N-ethyl-N′-(4-fluorophenyl) thiourea (16 g; 0.08 mol) in methylene chloride (200 mL). The mixture was heated at reflux for 1 hour then evaporated to dryness. Ethanol (200 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 (2×400 mL) then with water (400 mL). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was crystallized from ethyl acetate/hexane to give 19.1 g of 1-ethyl-3-(4-fluorophenyl)-2-thioxo-4,5-imidazolidinedione, m.p. 172–174° C. Mass spectrum; FAB (M+H)+ m/z 253. 1H-NMR (DMSO-d6; 300 MHz): δ 7.42–7.34 (m, 4H), 3.92 (q, 2H), and 1.22 ppm (t, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. customthen evaporated to dryness
  4. additionEthanol (200 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 (2×400 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-30b6d5849ea3420ba6e089b661af0d0b
Source dataset
uspto-grants-2006_11
Patent number
US07135492B2

Reaction notes

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