Ethoxalyl chloride → 3-[4,5-Dioxo-2-thioxo-3-(1,2,2-trimethyl-propyl)-imidazolidin-1-yl]-benzonitrile

HRID 1241616Notes

Reaction equation

HRID 1241616 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5]CC)=O.[C:9]([C:11]1[CH:12]=[C:13]([NH:17][C:18]([NH:20][CH:21]([CH3:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[S:19])[CH:14]=[CH:15][CH:16]=1)#[N:10]>ClCCl>[O:8]=[C:2]1[C:3](=[O:5])[N:17]([C:13]2[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=2)[C:9]#[N:10])[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 38203771-(3-Cyanophenyl)-3-(1,2,2-trimethyl-propyl)-thiourea

Product 1

HCID 101496903-[4,5-Dioxo-2-thioxo-3-(1,2,2-trimethyl-propyl)-imidazolidin-1-yl]-benzonitrileYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chlorooxoacetate (1.03 mL, 9.17 mmol) was added to a stirring solution of the above thiourea (1.19 g, 4.59 mmol) in dichloromethane (30 mL) and the resulting mixture was stirred overnight at room temperature. Concentration, trituration of the residue with diethyl ether, and filtration afforded 1.167 g (81%) of 3-[4,5-dioxo-2-thioxo-3-(1,2,2-trimethyl-propyl)-imidazolidin-1-yl]-benzonitrile as a yellow solid: mp 168.1–168.7° C.; 1H NMR (DMSO-d6): δ8.00 (d, 1H), 7.84 (s, 1H), 7.75 (m, 2H), 4.83 (q, 1H), 1.47 (d, 3H), 1.01 (s, 9H); IR (KBr): 3500, 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-e06c14735b0346888505d18c0c629c04
Source dataset
uspto-grants-2006_10
Patent number
US07115620B2

Reaction notes

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