Trifluoroacetic acid → HCID 16110250, compound

HRID 902151Notes

Reaction equation

HRID 902151 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.FC(F)(F)C(O)=O.[N+:19]([O-])([O-:21])=[O:20].[Na+]>>[NH2:1][C:2]1[C:11]([N+:19]([O-:21])=[O:20])=[CH:10][C:5]2[NH:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 24268Sodium NitrateHCID 8269896-amino-1,3-benzoxazol-2(3H)-one

Product 1

HCID 16110250HCID 16110250, compoundYield 96%

Procedure

To a solution of 2.0 g (13.3 mmol) of 6-amino-3H-benzoxazol-2-one [J. Chem. Soc., 321 (1938)] in 20 ml of trifluoroacetic acid 1.2 g (14.1 mmol) of sodium nitrate is added below 20° C. The reaction mixture is stirred at room temperature overnight, then concentrated. The residue is purified by column chromatography using Kieselgel 60 as adsorbent (Merck) and toluene:methanol=4:1 as eluent to yield 2.50 g (96%) of the title compound. Mp.: 198° C. (toluene-methanol).

Workup

  1. concentrationconcentrated
  2. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-3fa5bb826a6e41b2998b2212e2d3d1a1
Source dataset
uspto-grants-2008_04
Patent number
US07365083B2

Reaction notes

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