Ethoxalyl chloride → HCID 10149853, compound

HRID 1241614Notes

Reaction equation

HRID 1241614 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5]CC)=O.[CH2:9]([C:11]1[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[CH:13][C:12]=1[NH:19][C:20]([NH:22][C:23]([CH3:27])([CH3:26])[CH2:24][CH3:25])=[S:21])[CH3:10]>ClCCl>[CH3:27][C:23]([N:22]1[C:2](=[O:8])[C:3](=[O:5])[N:19]([C:12]2[CH:13]=[CH:14][C:15]([C:17]#[N:18])=[CH:16][C:11]=2[CH2:9][CH3:10])[C:20]1=[S:21])([CH3:26])[CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 21936578HCID 21936578, compound

Product 1

HCID 10149853HCID 10149853, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chlorooxoacetate (0.82 mL, 7.3 mmol) was added dropwise to a stirring solution of 1-(2-ethyl-4-cyanophenyl)-3-(1,1-dimethyl-propyl)-thiourea (1.0 g, 3.65 mmol) in dichloromethane (30 mL) and the resulting mixture was stirred at room temperature overnight. The mixture was concentrated to afford a residue which was triturated with diethyl ether and hexanes to afford 0.71 g (59%) of 4-[3-(1,1-dimethyl-propyl)-4,5-dioxo-2-thioxo-imidazolidin-1-yl]-3-ethyl-benzonitrile as a yellow solid: mp 172.8–173.3° C.; 1H NMR (DMSO-d6): δ 7.92 (s, 1H), 7.80 (d, 1H), 7.52 (d, 1H), 2.50 (m, 2H), 2.19 (m, 2H), 1.76 (2s, 6H), 1.08 (t, 3H), 0.85 (t, 3H); IR (KBr) 3400, 2950, 2260, 1775 cm−1; MS (m/z) 329 (M+).

Workup

  1. concentrationThe mixture was concentrated
  2. customto afford a residue which
  3. customwas triturated with diethyl ether and hexanes

Sources & evidence

ORD record
ord-aa9402241d2a4ee3a46cdcfbc7ff864f
Source dataset
uspto-grants-2006_10
Patent number
US07115620B2

Reaction notes

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