Nitrogen → TERT-BUTYL METHYL(3-NITROPHENYL)CARBAMATE

HRID 2274296Notes

Reaction equation

HRID 2274296 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].N#N.[H-].[Na+].[CH3:22]I>CN(C=O)C.O.CCCCCC.C(OCC)(=O)C>[CH3:22][N:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15]

Participants

8

Reactant 4

HCID 947NitrogenHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10514065Tert-butyl 3-nitrophenylcarbamate

Product 1

HCID 11528945TERT-BUTYL METHYL(3-NITROPHENYL)CARBAMATEYield 94.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of tert-butyl (3-nitrophenyl)carbamate (6.0 g) in DMF (35 mL) in a 100 mL 3-neck RBF equipped with N2 Bubbler and thermo pocket was added NaH (1.21 g) portion wise and stirred 1.0 hr at room temperature. Methyl iodide (5.37 g in 15 mL DMF) was added dropwise to the reaction mixture at 0° C. The mixture was allowed to cool to room temperature and stirred for 2 hr. The reaction was monitored on TLC using hexane:ethyl acetate (9:1) as mobile phase. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine solution, dried over sodium sulfate and concentrated completely under reduce pressure at 40° C. to give 6.0 g of tert-butyl methyl(3-nitrophenyl)carbamate 7. 1H NMR: DMSO-d6 (400 MHz): 1.43 (s, 9H), 3.26 (s, 3H), 7.62 (t, 1H, J=8.4), 7.77 (d, 1H, J=8), 8.00 (d, 1H, J=9.2), 8.18 (s, 1H).

Workup

  1. temperatureto cool to room temperature
  2. stirringstirred for 2 hr
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated completely
  8. customat 40° C.

Sources & evidence

ORD record
ord-adb15e4eb3ce4979b3406c5f17453d94
Source dataset
uspto-grants-2015_09
Patent number
US09126950B2

Reaction notes

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