Ethanol → HCID 13463001, compound

HRID 1270745Notes

Reaction equation

HRID 1270745 reaction equation
[Cl:1][C:2]1[C:3](C(O)=O)=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C([N:17]([CH2:20]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])=CC=1.[CH3:39][CH2:40][OH:41]>O1CCOCC1>[CH2:40]([O:41][C:20](=[O:29])[NH:17][C:3]1[C:2]([Cl:1])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)[CH3:39]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 134630003-Chloronaphthalene-2-carboxylic acid

Product 1

HCID 13463001HCID 13463001, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1.70 g of 3-chloro-2-naphthoic acid (8.23 mmol) in 50 mL of 1,4-dioxane is added 2.3 mL of triethylamine (16.45 mmol) followed by 2.7 mL of DPPA (12.34 mmol). The mixture is stirred for 2 hours at room temperature under an atmosphere of nitrogen. Then 4.8 mL (82.3 mmol) of EtOH is added and the reaction is heated to reflux and stirred for an additional 2 hours. The solvents are evaporated in vacuo and the remaining residue is dissolved in 50 mL of EtOAc and washed with 20 mL of 5% aqueous citric acid, 20 mL of 5% Na2CO3 and dried over MgSO4. The solvents are evaporated to give a residue that is purified by flash chromatography on silica gel (50% CH2Cl2/hexane) to give N-(3-chloro-2-naphthyl)carbamic acid ethyl ester as a yellow oil.

Workup

  1. temperaturethe reaction is heated
  2. temperatureto reflux
  3. stirringstirred for an additional 2 hours
  4. customThe solvents are evaporated in vacuo
  5. dissolutionthe remaining residue is dissolved in 50 mL of EtOAc
  6. washwashed with 20 mL of 5% aqueous citric acid, 20 mL of 5% Na2CO3
  7. dry with materialdried over MgSO4
  8. customThe solvents are evaporated
  9. customto give a residue that
  10. customis purified by flash chromatography on silica gel (50% CH2Cl2/hexane)

Sources & evidence

ORD record
ord-942cf92f0e114923b5e7632ddb740fcc
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

Loading…