Cyanuric chloride → s-Triazine, 4,6-dichloro-2-(N-methoxy-N-methylamino)-
Reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([Cl:9])[N:3]=1.Cl.[CH3:11][NH:12][O:13][CH3:14].CCN(C(C)C)C(C)C>CC(C)=O>[Cl:9][C:4]1[N:5]=[C:6]([Cl:8])[N:7]=[C:2]([N:12]([CH3:11])[O:13][CH3:14])[N:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2,4,6-Trichloro-1,3,5-triazine (XVIII) (30 g, 163 mmol) was dissolved in acetone (300 mL), and N,O-dimethylhydroxylamine hydrochloride (15.8 g, 163 mmol) and DIPEA (42 g, 326 mmol) were added and the mixture then stirred at 0° C. for 1 h. The solution was concentrated and the residue was treated with EtOAc (750 mL), washed with water (100 mL), and the organic layer was dried with Na2SO4. The volatiles were removed in vacuo and the residue was purified by flash column chromatography (pet ether/ethyl acetate=50/1 to 10/1) to yield the desired product, N-(4,6-dichloro[1,3,5]triazin-2-yl)-N,O-dimethyl-hydroxylamine (XXX), as a white solid (25 g, 73% yield). LCMS (ESI) m/z=210 (M+H)+.
Workup
- concentrationThe solution was concentrated
- additionthe residue was treated with EtOAc (750 mL)
- washwashed with water (100 mL)
- dry with materialthe organic layer was dried with Na2SO4
- customThe volatiles were removed in vacuo
- customthe residue was purified by flash column chromatography (pet ether/ethyl acetate=50/1 to 10/1)
Sources & evidence
- ORD record
- ord-47c7ad7c883a4f3cb3f682957adf796f
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09351972B2
Reaction notes
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