Oxalyl chloride → HCID 21893724, compound

HRID 720477Notes

Reaction equation

HRID 720477 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[CH3:7][S:8][C:9]1[CH:25]=[CH:24][CH:23]=[CH:22][C:10]=1[NH:11][C:12]([NH:14][O:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[S:13]>C(Cl)Cl>[CH3:7][S:8][C:9]1[CH:25]=[CH:24][CH:23]=[CH:22][C:10]=1[N:11]1[C:2](=[O:3])[C:1](=[O:5])[N:14]([O:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]1=[S:13]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 21893720HCID 21893720, compound

Product 1

HCID 21893724HCID 21893724, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (10.2 g; 0.08 mol) was added dropwise to the solution of ethyl 2-[({[2-(methylsulfanyl)anilino]carbothioyl}amino)oxy]acetate (12 g, 0.04 mol) in methylene chloride (100 mL). The mixture was heated at reflux for 1 hour then evaporated to dryness. The residue was treated with ethanol (100 mL) and the mixture was heated at reflux for 1 hour. The mixture was evaporated to dryness. The residue was chromatographed on silica gel (20%ethyl acetate in hexane). Ethyl 2-({3-[2-(methylsulfanyl)phenyl]-4,5-dioxo-2-thioxo-1-imidazolidinyl}oxy)acetate (4.7 g) was obtained as a solid, m.p. 112–114° C. Mass spectrum; (El, M.+) m/z 354. 1H-NMR (DMSO-d6; 300 MHz): δ 7.56–7.46 (m, 2H), 7.34 (m, 2H), 4.94 (q, 2H), 4.19 (q, 2H), 2.43 (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. additionThe residue was treated with ethanol (100 mL)
  5. temperaturethe mixture was heated
  6. temperatureat reflux for 1 hour
  7. customThe mixture was evaporated to dryness
  8. customThe residue was chromatographed on silica gel (20%ethyl acetate in hexane)

Sources & evidence

ORD record
ord-18e42f2ba6fb490c96ccb250dd2d4ca7
Source dataset
uspto-grants-2006_11
Patent number
US07135492B2

Reaction notes

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