Ethanol → N-(6-chloro-2-naphthyl)carbamic acid ethyl ester

HRID 1270771Notes

Reaction equation

HRID 1270771 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](C(O)=O)[CH:6]=[CH:5]2.C([N:17]([CH2:20]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])=CC=1.[CH2:39]([OH:41])[CH3:40]>O1CCOCC1>[CH2:39]([O:41][C:20](=[O:29])[NH:17][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[CH:8]=1)[CH3:40]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 132883276-Chloronaphthalene-2-carboxylic acid

Product 1

HCID 68803058N-(6-chloro-2-naphthyl)carbamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 6-chloro-2-naphthoic acid (1 g, 4.84 mmol) and triethylamine (1.35 mL, 9.68 mmol) in 1,4-dioxane (20 mL) at room temperature, is added DPPA (1.56 mL, 7.26 mmol). After stirring at room temperature for 2.5 hours, ethanol (2.82 mL, 48.4 mmol) is added and the reaction is heated to reflux temperature for 12 hours. After cooling to room temperature, the mixture is partitioned between EtOAc and water. The organic layer is washed with brine, dried (Na2SO4) and concentrated by rotary evaporator to give an oil. Flash chromatography on silica gel (3:1 hexanes/EtOAc) gives N-(6-chloro-2-naphthyl)carbamic acid ethyl ester as a white solid.

Workup

  1. temperaturethe reaction is heated
  2. temperatureto reflux temperature for 12 hours
  3. temperatureAfter cooling to room temperature
  4. customthe mixture is partitioned between EtOAc and water
  5. washThe organic layer is washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated by rotary evaporator
  8. customto give an oil

Sources & evidence

ORD record
ord-761ed3b65c7a4ce99bfd4fb4449fbdcb
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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