Water → tert-Butyl 2-(2-nitrophenylamino)ethylcarbamate

HRID 2267285Notes

Reaction equation

HRID 2267285 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C.O>O1CCCC1>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 738951-Fluoro-2-nitrobenzeneHCID 187201N-BOC-ethylenediamine

Product 1

HCID 47453724tert-Butyl 2-(2-nitrophenylamino)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-fluoro-2-nitrobenzene (2 g, 14.2 mmol), tert-butyl 2-aminoethylcarbamate (2.7 g, 17.0 mmol) and triethylamine (1.7 g, 2.4 mmol) in tetrahydrofuran was refluxed for 7 h. After cooling to rt 100 mL of water was added and the mixture was extracted with ethyl acetate (3×100 mL). The combined organic layer was washed with brine (150 mL), dried over anhydrous sodium sulfate and filtered. The solvent was removed and the product was used in the next step without further purification.

Workup

  1. temperaturewas refluxed for 7 h
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate (3×100 mL)
  4. washThe combined organic layer was washed with brine (150 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed
  8. customthe product was used in the next step without further purification

Sources & evidence

ORD record
ord-366af49cab344e688837a679a5878da8
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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