1-(3,4-dichlorophenyl)-2-methylsulfanyl-1H-imidazole-4,5-dione → HCID 178460300, compound

HRID 2212111Notes

Reaction equation

HRID 2212111 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[O:15])[N:11]=[C:10]2SC)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:18]([NH:21][C:22]([NH:24][C:25]([CH2:27][CH3:28])=[O:26])=[NH:23])([CH3:20])[CH3:19]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[O:15])[NH:11][C:10]2=[N:23][C:22]([NH:21][CH:18]([CH3:19])[CH3:20])=[N:24][C:25]([CH2:27][CH3:28])=[O:26])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 115873491-(3,4-dichlorophenyl)-2-methylsulfanyl-1H-imidazole-4,5-dioneHCID 178460305HCID 178460305, compound

Product 1

HCID 178460300HCID 178460300, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

Adapted the alternative method for the preparation of 4d as follows: To the solution of the crude dione 15 (0.413 g, 1.429 mmol) in 50 ml of dry CHCl3 was added N-isopropyl-N′-(ethylcarbonyl)guanidine (0.206 g, 1.191 mmol). The reaction mixture was heated at 50° C. for 48 hours. The reaction was quenched with water, extracted with chloroform and dried over Na2SO4. The solvent was removed in vacuo and the crude product was purified with a silica gel column using 3% EtOAc/CHCl3 as eluent to yield 4a as a white solid (0.115 g, 20%).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with chloroform
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed in vacuo
  5. customthe crude product was purified with a silica gel column

Sources & evidence

ORD record
ord-8e408b7bed464226a898618e525ea4f9
Source dataset
uspto-grants-2006_09
Patent number
US07101902B2

Reaction notes

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