Ethoxalyl chloride → 1-(5-Chloro-2-methylphenyl)-3-(2-propynyl)-2-thioxo-4,5-imidazolidinedione

HRID 720487Notes

Reaction equation

HRID 720487 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5]CC)=O.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:23])=[C:14]([NH:16][C:17]([NH:19][CH2:20][C:21]#[CH:22])=[S:18])[CH:15]=1>C(Cl)Cl>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:23])=[C:14]([N:16]2[C:2](=[O:8])[C:3](=[O:5])[N:19]([CH2:20][C:21]#[CH:22])[C:17]2=[S:18])[CH:15]=1

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 21893722N-(5-chloro-2-methylphenyl)-N'-(2-propynyl)thiourea

Product 1

HCID 102364291-(5-Chloro-2-methylphenyl)-3-(2-propynyl)-2-thioxo-4,5-imidazolidinedioneYield 20.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chlorooxoacetate (11.2 mL; 0.1 mol) was added dropwise while cooling in an ice bath to the stirring solution of N-(5-chloro-2-methylphenyl)-N′-(2-propynyl)thiourea (11.95 g; 0.05 mol) in methylene chloride (200 mL). The mixture was stirred for 18 hours at ambient temperature then evaporated to dryness. The residue was stirred in ether (200 mL) and the solids were collected by filtration and air dried to give 3.0 g 1-(5-chloro-2-methylphenyl)-3-(2-propynyl)-2-thioxo-4,5-imidazolidinedione, m.p. 162–164° C. Mass spectrum; (El, M.+) m/z 292/294. 1H-NMR (DMSO-d6; 300 MHz): δ 7.50–7.47 (m, 2H), 7.73 (d, 1H), 4.66 (q, 2H), 3.37 (t, 1H), and 2.15 ppm (s,3H).

Workup

  1. customthen evaporated to dryness
  2. stirringThe residue was stirred in ether (200 mL)
  3. filtrationthe solids were collected by filtration and air
  4. customdried

Sources & evidence

ORD record
ord-e2678460f8a947718c15b9a41a0b538c
Source dataset
uspto-grants-2006_11
Patent number
US07135492B2

Reaction notes

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