Dimethyl Sulfate → HCID 57974577, compound

HRID 1864661Notes

Reaction equation

HRID 1864661 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[NH:11][C:12](=[O:16])[O:13][CH2:14][CH3:15].[C:17](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[N:11]([CH3:17])[C:12](=[O:16])[O:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 57974482HCID 57974482, compound

Product 1

HCID 57974577HCID 57974577, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Ethyl 4-chloro-2-nitropyridin-3-yl-carbamate (350 mg, 1.4 mmol) was dissolved in acetone and potassium carbonate (280 mg, 2 mmol) was added followed by dimethyl sulfate (161 μL, 1.7 mmol). The reaction mixture was heated to reflux for 5 hours, cooled at room temperature, diluted with water and extracted with DCM. The organic layer was dried and evaporated to afford the title compound (340 mg, 93%). 1H-NMR (δ, ppm, DMSO-d6): 1.02+1.25 (t+t, rotamers, 3H, CH3,Et), 3.14+3.19 (s+s, rotamers, 3H, NCH3), 4.05+4.14 (q+q, rotamers, 2H, CH2,Et), 8.21 (d, 1H, HPy,5, J=5.70 Hz), 8.60 (d, 1H, HPy,6, J=5.20 Hz). LC-MS (m/z): 259 (M+H, 100).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 hours
  3. extractionextracted with DCM
  4. customThe organic layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-b29a2b604ce34089bfa9c822bedd05f4
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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