Potassium Carbonate → HCID 10192929, compound

HRID 1241631Notes

Reaction equation

HRID 1241631 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5]CC)=O.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]([NH:18][CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[S:17])[CH:10]=1.C([O-])([O-])=O.[K+].[K+]>ClCCl>[CH3:21][C:20]([CH3:23])([CH3:22])[CH2:19][N:18]1[C:2](=[O:8])[C:3](=[O:5])[N:15]([C:11]2[CH:10]=[N:9][CH:14]=[CH:13][CH:12]=2)[C:16]1=[S:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 20884Ethoxalyl chlorideHCID 3042815N'-(2,2-Dimethylpropyl)-N-pyridin-3-ylcarbamimidothioic acid

Product 1

HCID 10192929HCID 10192929, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chlorooxoacetate (0.33 mL, 2.90 mmol) was added to a stirring solution of the above thiourea (0.50 g, 2.24 mmol) and K2CO3 (0.31 g) 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 0.50 g (81%) 1-(2,2-dimethyl-propyl)-3-pyridin-3-yl-2-thioxo-imidazolidine-4,5-dione as a yellow solid: mp 111.4–112.8° C.; IR (KBr): 3500, 2980, 1770 cm1; MS (m/z) 378 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-949f6ef1248e4949b8f927b5077a399f
Source dataset
uspto-grants-2006_10
Patent number
US07115620B2

Reaction notes

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