Cyanuric chloride → 1-[(4,6-Dichloro-1,3,5-triazin-2-yl)amino]imidazolidine-2,4-dione

HRID 76331Notes

Reaction equation

HRID 76331 reaction equation
Cl.[NH2:2][N:3]1[CH2:9][C:7](=[O:8])[NH:6][C:4]1=[O:5].[N:10]1[C:17]([Cl:18])=[N:16][C:14](Cl)=[N:13][C:11]=1[Cl:12].C(=O)(O)[O-].[Na+]>C(#N)C>[Cl:12][C:11]1[N:10]=[C:17]([Cl:18])[N:16]=[C:14]([NH:2][N:3]2[CH2:9][C:7](=[O:8])[NH:6][C:4]2=[O:5])[N:13]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 516892Sodium BicarbonateHCID 124729631-Aminohydantoin hydrochloride

Product 1

HCID 866980651-[(4,6-Dichloro-1,3,5-triazin-2-yl)amino]imidazolidine-2,4-dioneYield 107.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

An ice-cold suspension of 1-aminohydantoin hydrochloride (457 mg, 3.0 mmol), cyanuric chloride (500 mg, 2.73 mmol) and sodium bicarbonate (505 mg, 6 mmol) in acetonitrile (5 mL) was stirred under an atmosphere of nitrogen for 2 h and then stirred at room temperature for 20 h. The reaction mixture was evaporated to dryness under reduced pressure and the residue was extracted with ethyl acetate and the ethyl acetate was separated and dried (MgSO4). The crude product (770 mg) gave a single spot on thin layer chromatography [silica; CH2Cl2/MeOH (10:1)] and was used in the next step without further purification. NMR (CD3CN): δ=4.11 (s, 2H); 8.71 (s, 1H); 8.85 (s, 1H).

Workup

  1. stirringstirred at room temperature for 20 h
  2. customThe reaction mixture was evaporated to dryness under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate
  4. customthe ethyl acetate was separated
  5. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-1eddf919437649cab3c98bfcaf8416ae
Source dataset
uspto-grants-2014_09
Patent number
US08835629B2

Reaction notes

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