Water → 2-Ethyl-4,7-benzoxazoledione

HRID 1727240Notes

Reaction equation

HRID 1727240 reaction equation
FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=[O:4].[CH2:22]([C:24]1[O:25][C:26]2[C:27](=[C:29](N)[CH:30]=[CH:31][CH:32]=2)[N:28]=1)[CH3:23].[OH2:34]>C(#N)C.C(#N)C.O.C(OC(C)C)(C)C>[CH2:22]([C:24]1[O:34][C:29]2[C:30](=[O:4])[CH:31]=[CH:32][C:26](=[O:25])[C:27]=2[N:28]=1)[CH3:23]

Participants

7

Reactant 3

HCID 962Water2×HCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 120715892-Ethyl-1,3-benzoxazol-4-amine

Product 1

HCID 120715902-Ethyl-4,7-benzoxazoledione

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 7914Diisopropyl EtherSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
-5 °C

Procedure

A solution of [bis(trifluoroacetoxy)iodo]benzene (2.2 eq.) in a mixture of acetonitrile and water (80/20) is added dropwise to a solution of 2-ethyl-1,3-benzoxazol-4-amine (1 eq.) in the same acetonitrile/water mixture maintained at −5° C. The reaction medium is then diluted with water followed by extracting with dichloromethane. The resulting organic phase is washed with water, followed by drying over sodium sulphate and concentrating in order to produce a brown paste. Purification by medium pressure chromatography on silica gel produces, after taking up in diisopropyl ether, a yellow crystalline solid. Melting point: 99° C.

Workup

  1. extractionby extracting with dichloromethane
  2. washThe resulting organic phase is washed with water
  3. dry with materialby drying over sodium sulphate
  4. concentrationconcentrating in order
  5. customto produce a brown paste
  6. customPurification by medium pressure chromatography on silica gel
  7. customproduces

Sources & evidence

ORD record
ord-ecd578abf75749c6a5e3b351c760ec2e
Source dataset
uspto-grants-2009_02
Patent number
US07495021B2

Reaction notes

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