Ethoxalyl chloride → 1-(2,4-Difluoro-phenyl)-3-(2,2-dimethyl-propyl)-2-thioxo-imidazolidine-4,5-dione

HRID 1241624Notes

Reaction equation

HRID 1241624 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5]CC)=O.[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[NH:17][C:18]([NH:20][CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[S:19]>ClCCl>[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[N:17]1[C:2](=[O:8])[C:3](=[O:5])[N:20]([CH2:21][C:22]([CH3:24])([CH3:23])[CH3:25])[C:18]1=[S:19]

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 219365771-(2,4-Difluoro-phenyl)-3-(2,2-dimethylpropyl)-thiourea

Product 1

HCID 101496661-(2,4-Difluoro-phenyl)-3-(2,2-dimethyl-propyl)-2-thioxo-imidazolidine-4,5-dioneYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chlorooxoacetate (0.57 mL, 5.03 mmol) was added to a stirring solution of the above thiourea (1.00 g, 3.87 mmol) in dichloromethane (15 mL) and the resulting mixture was stirred overnight at room temperature. Concentration, trituration of the residue with diethyl ether, and recrystallization from boiling methanol afforded 0.66 g (55%) of 1-(2,4-difluoro-phenyl)-3-(2,2-dimethyl-propyl)-2-thioxo-imidazolidine-4,5-dione as a yellow solid: mp 156.2–156.9° C.; 1H NMR (DMSO-d6): δ 7.55 (m, 2H), 7.30 (m, 1H), 3.76 (m, 2H), 0.95 (s, 9H); IR (KBr): 3510 2920, 2230, 1775 cm1; MS (m/z) 312 (M+).

Workup

  1. concentrationConcentration, trituration of the residue
  2. customwith diethyl ether, and recrystallization

Sources & evidence

ORD record
ord-55306a01b4794eb3ba1ab7c822bd1ed8
Source dataset
uspto-grants-2006_10
Patent number
US07115620B2

Reaction notes

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