Ethoxalyl chloride → HCID 10193692, compound

HRID 720476Notes

Reaction equation

HRID 720476 reaction equation
Cl[C:2](=[O:8])[C:3](OCC)=[O:4].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:27])=[C:14]([CH:26]=1)[NH:15][C:16]([NH:18][O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[S:17]>C(Cl)Cl>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:27])=[C:14]([N:15]2[C:3](=[O:4])[C:2](=[O:8])[N:18]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]2=[S:17])[CH:26]=1

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 21893723HCID 21893723, compound

Product 1

HCID 10193692HCID 10193692, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chlorooxoacetate (11.1 mL; 0.1 mol) was added dropwise to the solution of ethyl 2-({[(5-chloro-2-methylanilino) carbothioyl]amino}oxy)acetate (15.1 g; 0.05 mol) in methylene chloride (200 mL). The mixture was heated at reflux for 1 hour then evaporated to dryness. The residue was stirred in ether for 15 minutes and the solids were filtered. The solids were washed with fresh ether and dried to give 13.1 g of ethyl 2-{[3-(5-chloro-2-methylphenyl)-4,5-dioxo-2-thioxo-1-imidazolidinyl]oxy}acetate as a solid, m.p. 157–159° C. Mass spectrum; FAB (M+H)+ m/z 357. 1H-NMR (DMSO-d6; 300 MHz): δ 7.50 (d, 1H), 7.42 (m, 2H), 4.90 (q, 2H), 4.20 (q, 2H), 2.17 (s, 3H), and 1.24 ppm (t, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. customthen evaporated to dryness
  4. filtrationthe solids were filtered
  5. washThe solids were washed with fresh ether
  6. customdried

Sources & evidence

ORD record
ord-0c0d4c78b8ee4599900d66609a7b6c69
Source dataset
uspto-grants-2006_11
Patent number
US07135492B2

Reaction notes

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