Methyl iodide → HCID 59128268, compound

HRID 1990977Notes

Reaction equation

HRID 1990977 reaction equation
[CH3:1][O:2][C:3](=[O:16])[NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1.[CH3:17]C([O-])(C)C.[K+].CI>C1COCC1.O>[CH3:17][N:4]([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[C:3](=[O:16])[O:2][CH3:1]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 59128265HCID 59128265, compound

Product 1

HCID 59128268HCID 59128268, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl[2-(4-nitrophenyl)ethyl]carbamate (224 mg, 1 mmol) in THF (2 mL) was added KOtBu (201 mg, 1.8 mmol) and MeI (256 mg, 1.8 mmol) sequentially. The reaction mixture was stirred for 12 hours at room temperature. The reaction was diluted with water (5 mL), extracted with EtOAc (2×15 mL), washed with water (5 mL), dried (MgSO4), filtered and concentrated under reduced pressure. Silica gel chromatography (60% ethyl acetate/hexane) afforded the title compound as a semi solid (160 mg, 67.2%). MS (ES+): 239 (M+H).

Workup

  1. extractionextracted with EtOAc (2×15 mL)
  2. washwashed with water (5 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e2ef7a6d957a47a6a32cb31d1c55b1be
Source dataset
uspto-grants-2010_01
Patent number
US07645752B2

Reaction notes

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