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

HRID 2388103Notes

Reaction equation

HRID 2388103 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>[F:18][C:19]1[CH:29]=[CH:28][C:22]([O:23][CH2:24][CH2:25][CH2:26][NH:27][C:8](=[O:16])[O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:21]([N+:30]([O-:32])=[O:31])[CH:20]=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-c675ada9b9354fe89b7d9733d4723069
Source dataset
uspto-grants-2012_09
Patent number
US08269011B2

Reaction notes

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