Potassium Carbonate → (S)-3-(2-Amino-3-nitrophenoxy)-1,2-epoxypropane

HRID 1601454Notes

Reaction equation

HRID 1601454 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[CH2:12]1[O:14][C@@H:13]1[CH2:15]OS(C1C=C([N+]([O-])=O)C=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH2:15][C@H:13]1[O:14][CH2:12]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 15049327(S)-3-(2-Amino-3-nitrophenoxy)-1,2-epoxypropane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-amino-3-nitrophenol (5.95 g, 38.6 mmol) and (2S)-(+)-glycidyl 3-nitrobenzenesulfonate (10.0 g, 38.6 mmol) in 150 mL of acetone was treated with 1.1 equivalents of K2CO3 (5.86 g, 42.4 mmol) and stirred at reflux for 18 hours. The suspension was cooled to ambient temperature; the solids were filtered; and the filtrate concentrated in vacuo to dryness. The resulting solids were partitioned between chloroform and water, and the aqueous layer extracted once with chloroform. The organic layers were combined and dried over Na2SO4 and concentrated in vacuo to 8.0 g (99%) of an orange solid. TLC (Rf =0.5, CHCl3) and NMR indicated >95% purity, so the material was used without further purification. NMR.

Workup

  1. temperatureat reflux for 18 hours
  2. filtrationthe solids were filtered
  3. concentrationand the filtrate concentrated in vacuo to dryness
  4. customThe resulting solids were partitioned between chloroform and water
  5. extractionthe aqueous layer extracted once with chloroform
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo to 8.0 g (99%) of an orange solid
  8. customso the material was used without further purification

Sources & evidence

ORD record
ord-3b46f3ff9c914b6fa91f3f10fd69a7ae
Source dataset
uspto-grants-1999_11
Patent number
US05977154

Reaction notes

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