Ethoxalyl chloride → HCID 10171660, compound

HRID 1241612Notes

Reaction equation

HRID 1241612 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][C:21]([CH3:24])([CH3:23])[CH3:22])=[S:19])=[CH:13][CH:12]=1)#[N:10]>ClCCl>[C:21]([N:20]1[C:2](=[O:8])[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]1=[S:19])([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 21936581HCID 21936581, compound

Product 1

HCID 10171660HCID 10171660, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chlorooxoacetate (1.15 mL, 10.29 mmol) was added dropwise to a stirring solution of 1-(4-cyanophenyl)-3-(tert-butyl)-thiourea (0.802 g, 3.25 mmol) in dichloromethane (40 mL) and the resulting mixture was stirred at room temperature overnight. The mixture was concentrated to afford a residue which was purified by flash column chromatography (50% ethyl acetate/hexanes) to afford 0.48 g (32%) of 4-[3-(tert-butyl)-4,5-dioxo-2-thioxo-imidazolidin-1-yl]-benzonitrile as a yellow solid: mp 200.4–201.3° C.; 1H NMR (DMSO-d6): δ 8.00 (d, 2H), 7.52 (d, 2H), 2.20 (q, 2H), 1.79 (s, 9H); IR (KBr) 3500, 2220, 1760 cm−1; MS (m/z) 287 (M+).

Workup

  1. concentrationThe mixture was concentrated
  2. customto afford a residue which
  3. customwas purified by flash column chromatography (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-291c337902884cd6aa25e3217b863f13
Source dataset
uspto-grants-2006_10
Patent number
US07115620B2

Reaction notes

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