Ethoxalyl chloride → HCID 10125764, compound

HRID 1241626Notes

Reaction equation

HRID 1241626 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5]CC)=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([NH:19][CH:20]([CH3:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[S:18])=[CH:12][CH:11]=1>ClCCl>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([N:16]2[C:2](=[O:8])[C:3](=[O:5])[N:19]([CH:20]([CH3:25])[C:21]([CH3:23])([CH3:22])[CH3:24])[C:17]2=[S:18])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 3611988HCID 3611988, compound

Product 1

HCID 10125764HCID 10125764, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chlorooxoacetate (0.62 mL, 5.60 mmol) was added to a stirring solution of the above thiourea (1.00 g, 3.72 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 0.72 g (60%) of 1-(4-chloro-phenyl)-2-thioxo-3-(1,2,2-trimethyl-propyl)-imidazolidine-4,5-dione as a yellow solid: mp 198.8–199.5° C.; 1H NMR (DMSO-d6): δ 7.61 (d, 2H), 7.40 (d, 2H), 4.82 (q, 1H), 1.45 (d, 3H), 0.98 (s, 9H); IR (KBr): 3500, 2920, 1775 cm1; MS (m/z) 324 (M+).

Workup

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

Sources & evidence

ORD record
ord-295e4532b0014f25ac6b29e56aa10f33
Source dataset
uspto-grants-2006_10
Patent number
US07115620B2

Reaction notes

Loading…