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

HRID 1241622Notes

Reaction equation

HRID 1241622 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][CH:21]([CH3:26])[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]([CH:21]([CH3:26])[C:22]([CH3:24])([CH3:23])[CH3:25])[C:18]1=[S:19]

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 219365791-(2,4-Difluoro-phenyl)-3-(1,2,2-trimethyl-propyl)-thiourea

Product 1

HCID 101720151-(2,4-Difluoro-phenyl)-2-thioxo-3-(1,2,2-trimethyl-propyl)-imidazolidine-4,5-dioneYield 62.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chlorooxoacetate (0.53 mL, 4.77 mmol) was added to a stirring solution of the above thiourea (1.00 g, 3.67 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 0.75 g (62%) of 1-(2,4-difluoro-phenyl)-2-thioxo-3-(1,2,2-trimethyl-propyl)-imidazolidine-4,5-dione as a yellow solid: mp 155.2–156.0° C.; 1H NMR (DMSO-d6): δ 7.55 (m, 2H), 7.30 (m, 1H), 4.80 (m, 1H), 1.51 (d, 3H), 0.99 (s, 9H); IR (KBr): 3550, 2970, 2230, 1770 cm1; MS (m/z) 326 (M+).

Workup

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

Sources & evidence

ORD record
ord-5cf13dfbb7d6432f96fe5222b36d5a55
Source dataset
uspto-grants-2006_10
Patent number
US07115620B2

Reaction notes

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