Ethoxalyl chloride → HCID 10286450, compound

HRID 1241610Notes

Reaction equation

HRID 1241610 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5]CC)=O.[C:9]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][CH:21]([CH3:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[S:19])=[CH:13][CH:12]=1)#[N:10]>ClCCl>[O:8]=[C:2]1[C:3](=[O:5])[N:17]([C:14]2[CH:13]=[CH:12][C:11]([C:9]#[N:10])=[CH:16][CH:15]=2)[C:18](=[S:19])[N:20]1[CH:21]([CH3:26])[C:22]([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 21936583HCID 21936583, compound

Product 1

HCID 10286450HCID 10286450, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chlorooxoacetate (5.60 mL, 50.0 mmol) was added to a stirring solution of the above thiourea (6.54 g, 25.0 mmol) in dichloromethane (170 mL) and the resulting mixture was stirred overnight at room temperature. Concentration, trituration of the residue with diethyl ether, and filtration afforded 5.77 g (73%) of 4-[4,5-dioxo-2-thioxo-3-(1,2,2-trimethyl-propyl)-imidazolidin-1-yl]-benzonitrile as a yellow solid: mp 219.6–219.9° C.; 1H NMR (DMSO-d6): δ 8.03 (d, 2H), 7.60 (d, 2H), 4.82 (q, 1H), 1.47 (d, 3H), 1.00 (s, 9H); IR (KBr): 3505, 2970, 2230, 1765, 1600 cm−1; MS (m/z) 315 (M+).

Workup

  1. concentrationConcentration, trituration of the residue
  2. filtrationwith diethyl ether, and filtration

Sources & evidence

ORD record
ord-6eb28902fb8b4d2fb5ace7a162eaa525
Source dataset
uspto-grants-2006_10
Patent number
US07115620B2

Reaction notes

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