Triethylamine → Phenyl[3-(4-fluoro-2-nitrophenoxy)propyl]carbamate

HRID 1477121Notes

Reaction equation

HRID 1477121 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:16])[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[F:18][C:19]1[CH:29]=[CH:28][C:22]([O:23][CH2:24][CH2:25][CH2:26][NH2:27])=[C:21]([N+:30]([O-:32])=[O:31])[CH:20]=1>O1CCOCC1>[C:10]1([O:9][C:8](=[O:16])[NH:27][CH2:26][CH2:25][CH2:24][O:23][C:22]2[CH:28]=[CH:29][C:19]([F:18])=[CH:20][C:21]=2[N+:30]([O-:32])=[O:31])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 623484053-(4-Fluoro-2-nitrophenoxy)propylamine

Product 1

HCID 86641934Phenyl[3-(4-fluoro-2-nitrophenoxy)propyl]carbamateYield 94.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Triethylamine (2.90 ml, 21.4 mmol) and phenyl chlorocarbonate (2.52 ml, 20.0 mmol) were added to a dioxane solution (43 ml) of 3-(4-fluoro-2-nitrophenoxy)propylamine (4.03 g, 18.8 mmol), while being cooled with ice, and the mixture was stirred at room temperature for 0.5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was then purified by silica gel column chromatography (dichloromethane:ethyl acetate=30:1). The purified product was concentrated to dryness under reduced pressure to thereby obtain 5.92 g of powdery yellow phenyl[3-(4-fluoro-2-nitrophenoxy)propyl]carbamate (yield: 94%).

Workup

  1. temperaturewhile being cooled with ice
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was then purified by silica gel column chromatography (dichloromethane:ethyl acetate=30:1)
  4. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-128e26eee526476b83d0dec4424bced4
Source dataset
uspto-grants-2016_08
Patent number
US09403773B2

Reaction notes

Loading…