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

HRID 76336Notes

Reaction equation

HRID 76336 reaction equation
[NH2:1][CH:2]1[NH:6][C:5](=[O:7])[N:4]([CH3:8])[C:3]1=[O:9].[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:1][CH:2]2[NH:6][C:5](=[O:7])[N:4]([CH3:8])[C:3]2=[O:9])[N:13]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 516892Sodium BicarbonateHCID 552819085-Amino-3-methyl-imidazolidine-2,4-dione

Product 1

HCID 866980675-(4,6-Dichloro-[1,3,5]triazin-2-ylamino)-3-methyl-imidazolidine-2,4-dioneYield 78.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

An ice-cold suspension of 5-amino-3-methyl-imidazolidine-2,4-dione (Example 1.3, Part C) (266 mg, 2.06 mmol), cyanuric chloride (415 mg, 2.27 mmol) and sodium bicarbonate (191 mg, 2.27 mmol) in acetonitrile (15 mL) was stirred over an ice bath under a nitrogen atmosphere for 1 h, and then allowed to stir at room temperature for 22 h. The solvent was evaporated, and the crude product was extracted with ethyl acetate. The organic layer was dried and evaporated, and the crude product was purified by column chromatography (PS with gradient elution to DCM:EtOAc 1:1) to afford the product as a cream solid (448 mg, 78%). δH (300 MHz, CD3CN) 7.50 (br s, 1H, NH), 6.56 (br s, 1H, NH), 5.60 (dd, J 7.8, 1.8 Hz, 1H, CH), 2.97 (s, 3H, CH3). Mass spectrum (ESI) m/z 259 [M+H(OH for Cl exchanged ion)].

Workup

  1. stirringto stir at room temperature for 22 h
  2. customThe solvent was evaporated
  3. extractionthe crude product was extracted with ethyl acetate
  4. customThe organic layer was dried
  5. customevaporated
  6. customthe crude product was purified by column chromatography (PS with gradient elution to DCM:EtOAc 1:1)

Sources & evidence

ORD record
ord-0ed3e78492234444ae0801c01b183fb2
Source dataset
uspto-grants-2014_09
Patent number
US08835629B2

Reaction notes

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