Cyanuric chloride → 5-(4,6-Dichloro-[1,3,5]triazin-2-ylamino)-3-methyl-imidazolidine-2,4-dione
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]=1Participants
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
- stirringto stir at room temperature for 22 h
- customThe solvent was evaporated
- extractionthe crude product was extracted with ethyl acetate
- customThe organic layer was dried
- customevaporated
- customthe crude product was purified by column chromatography (PS with gradient elution to DCM:EtOAc 1:1)
Sources & evidence
- ORD record
- ord-faa0b04542c84cd58ec5d77b64f89607
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221799B2
Reaction notes
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