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

HRID 238315Notes

Reaction equation

HRID 238315 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-ec5108af1df542c88c0e0d3b2918c4fe
Source dataset
uspto-grants-2014_02
Patent number
US08642619B2

Reaction notes

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