Ethoxalyl chloride → HCID 10126274, compound

HRID 1241618Notes

Reaction equation

HRID 1241618 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5]CC)=O.[Br: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>[Br: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 21936576HCID 21936576, compound

Product 1

HCID 10126274HCID 10126274, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chlorooxoacetate (0.496 mL, 4.44 mmol) was added to a stirring solution of the above thiourea (0.70 g, 2.22 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 0.647 g (79%) of 1-(4-bromo-phenyl)-2-thioxo-3-(1,2,2-trimethyl-propyl)-imidazolidine-4,5-dione as a yellow solid: mp 207.1–207.9° C.; 1H NMR (DMSO-d6): δ 7.74 (d, 1H), 7.32 (d, 2H), 4.81 (q, 1H), 1.48 (d, 3H), 0.99 (s, 9H); IR (KBr): 3500, 2970, 2230, 1770, 1500 cm−1; MS (m/z) 368 (M+).

Workup

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

Sources & evidence

ORD record
ord-cb756d3b72154454b40b610c921cb407
Source dataset
uspto-grants-2006_10
Patent number
US07115620B2

Reaction notes

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