Water → Tert-butyl 3-nitrophenylcarbamate

HRID 1482713Notes

Reaction equation

HRID 1482713 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].[O:11](C(OC(C)(C)C)=O)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=O.CCCCCC.C(OCC)(=O)C.O>C1COCC1.CN(C1C=CN=CC=1)C>[C:15]([O:14][C:12](=[O:11])[NH:7][C:6]1[CH:8]=[CH:9][CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 74233-NitroanilineHCID 90495Di-tert-butyl dicarbonateHCID 21226206Ethyl acetate hexane

Product 1

HCID 10514065Tert-butyl 3-nitrophenylcarbamateYield 82.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a 50 mL 3-neck RBF, 3-nitroaniline 5 (5.0 g) in THF (40 mL) and (BOC)2O (7.89 g) was charged and cooled to 0° C. DMAP (6.09 g) was added portion-wise into the reaction mixture and reaction mixture was warmed to room temperature and stirred at room temperature for 5 hr. The reaction was monitored on TLC using hexane:ethyl acetate (5:5) 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 50 mL brine solution, dried over sodium sulfate and concentrated completely under reduced pressure at 40° C. Crude material was purified by using column chromatography. Product was eluted with 4% ethyl acetate in hexane and concentrated to give 7.1 g of tert-butyl(3-nitrophenyl)carbamate.

Workup

  1. custominto the reaction mixture and reaction mixture
  2. temperaturewas warmed to room temperature
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with 50 mL brine solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated completely under reduced pressure at 40° C
  8. customCrude material was purified
  9. washProduct was eluted with 4% ethyl acetate in hexane
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c622b8bff9974e73880f5dbd1e321cd1
Source dataset
uspto-grants-2016_08
Patent number
US09415049B2

Reaction notes

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