Ethoxalyl chloride → HCID 10215432, compound

HRID 1241627Notes

Reaction equation

HRID 1241627 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5]CC)=O.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][CH:23]([CH3:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[S:21])=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>ClCCl>[C:9]([C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:2](=[O:8])[C:3](=[O:5])[N:22]([CH:23]([CH3:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:20]2=[S:21])=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 21936580HCID 21936580, compound

Product 1

HCID 10215432HCID 10215432, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chlorooxoacetate (0.46 mL, 4.10 mmol) was added to a stirring solution of the above thiourea (0.80 g, 2.74 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 0.61 g (64%) of 1-(4-tert-butyl-phenyl)-2-thioxo-3-(1,2,2-trimethyl-propyl)-imidazolidine-4,5-dione as a yellow solid: mp 208.9–209.5° C.; 1H NMR (DMSO-d6): δ 7.52 (d, 2H), 7.40 (d, 2H), 4.85 (q, 1H), 1.48 (d, 3H), 1.30 (s, 9H), 1.00 (s, 9H); IR (KBr): 3505, 2930, 1780 cm1; MS (m/z) 346 (M+).

Workup

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

Sources & evidence

ORD record
ord-63be775197f34eabbfdb13cc8598ba9f
Source dataset
uspto-grants-2006_10
Patent number
US07115620B2

Reaction notes

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