Homoserine lactone hydrobromide → 3-[(diphenylmethylene)amino]dihydrofuran-2(3H)-one

HRID 1160178Notes

Reaction equation

HRID 1160178 reaction equation
Br.[NH2:2][CH:3]1[CH2:7][CH2:6][O:5][C:4]1=[O:8].[C:9](=N)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl.O>[C:10]1([C:9](=[N:2][CH:3]2[CH2:7][CH2:6][O:5][C:4]2=[O:8])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 73508Homoserine lactone hydrobromideHCID 136809Benzophenone imine

Product 1

HCID 132309163-[(diphenylmethylene)amino]dihydrofuran-2(3H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-aminodihydrofuran-2(3H)-one hydrobromide (5 g, 27.5 mmol) in DCM (50 mL) was added benzophenone imine (5 g, 27.5 mmol) and the reaction mixture was stirred at RT for 3 days. The reaction mixture was diluted with water and DCM, the organic layer was extracted, washed with aquous sodium bicarbonate, brine, dried over sodium sulfate and concentrated in vacuo to give 3-[(diphenylmethylene)amino]dihydrofuran-2(3H)-one as a thick colorless gel which crystallized to a white solid.

Workup

  1. extractionthe organic layer was extracted
  2. washwashed with aquous sodium bicarbonate, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95eaa75900204f5e964d4099a0b5613c
Source dataset
uspto-grants-2010_10
Patent number
US07816378B2

Reaction notes

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