2-Aminobenzophenone → 2-(5-Oxotetrahydrofuran-2-carbonyl)aminobenzophenone

HRID 1774

Reaction equation

HRID 1774 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[C:16](=[O:19])([O-])[OH:17].[Na+]>C(OCC)(=O)C>[O:19]=[C:16]1[O:17][CH:3]([C:4]([NH:1][C:2]2[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=2[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:5])=[O:5])[CH2:2][CH2:15]1

Participants

4

Reactant 2

HCID 760802-AminobenzophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 539323702-(5-Oxotetrahydrofuran-2-carbonyl)aminobenzophenone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4.9 g of 5-oxotetrahydrofuran-2-carboxylic acid and 5.5 ml of thionyl chloride was subjected to reflux for 2 hours. Thionyl chloride was then distilled off under reduced pressure to leave 5-oxotetrahydrofuran-2-carbonyl chloride. This product was mixed with 5.0 g of 2-aminobenzophenone, 200 ml of ethyl acetate and 200 ml of a saturated aqueous solution of sodium hydrogencarbonate, which was stirred for one hour at room temperature. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate, then the solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluent, hexane:ethyl acetate=2:1) to give 2-(5-oxotetrahydrofuran-2-carbonyl)aminobenzophenone (6.5 g) as needles, m.p. 100° C.-102° C.

Workup

  1. washThe ethyl acetate layer was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by means of a silica gel column chromatography (eluent, hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-947d3e4afae94a0b8dd4f97535b58d90
Source dataset
uspto-grants-1998_03
Patent number
US05726306

Linked notes

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