Methyl iodide → HCID 86665978, compound

HRID 530063Notes

Reaction equation

HRID 530063 reaction equation
[CH:1]([O:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:3])[CH3:2].[C:16]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH:1]([O:4][N:5]([CH3:16])[C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86665979HCID 86665979, compound

Product 1

HCID 86665978HCID 86665978, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

An ACE® pressure tube was charged with benzyl isopropoxycarbamate (4.98 g, 23.80 mmol), anhydrous K2CO3 (4.94 g, 35.70 mmol), methyl iodide (6.7 mL, 107.10), and anhydrous acetone (30 mL). The reaction mixture was heated at 70° C. for 24 h. The reaction mixture was filtered, and the acetone was evaporated. The resulting slurry was dissolved in EtOAc, washed with water (3×50 mL), dried (Na2SO4), and filtered. The solvent was removed to yield benzyl isopropoxy(methyl)carbamate (4.96 g, 93%). 400 MHz 1H-NMR (DMSO-d6, ppm) 7.41-7.30 (5H, m), 5.12 (2H, s), 4.08 (1H, septet, J=6.2 Hz), 3.08 (3H, s), 1.12 (6H, d, J=6.2 Hz).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe acetone was evaporated
  3. dissolutionThe resulting slurry was dissolved in EtOAc
  4. washwashed with water (3×50 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-3bb6b4520341411f80a05bc6ff65df44
Source dataset
uspto-grants-2016_05
Patent number
US09351972B2

Reaction notes

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