Hydrochloric Acid → 3-amino-3-benzyldihydrofuran-2(3H)-one

HRID 1160180Notes

Reaction equation

HRID 1160180 reaction equation
[CH2:1]([C:8]1([N:14]=C(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:12][CH2:11][O:10][C:9]1=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO.C1COCC1>[NH2:14][C:8]1([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:12][CH2:11][O:10][C:9]1=[O:13]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 866323393-benzyl-3-[(diphenylmethylene)amino]dihydrofuran-2(3H)-one

Product 1

HCID 140831243-amino-3-benzyldihydrofuran-2(3H)-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-benzyl-3-[(diphenylmethylene)amino]dihydrofuran-2(3H)-one (5.67 g, 15.95 mmol) in MeOH (50 mL) and THF (50 mL) was added 6N HCl (5.3 mL, 32 mmol). After 5 min stirring at RT, the reaction mixture was concentrated in vacuo, diluted with water and benzophenone was extracted with diethyl ether (3×). The aqueous layer was basified to pH 10 with 6N NaOH, extracted with DCM (×2), dried over sodium sulfate and concentrated in vacuo to give 3-amino-3-benzyldihydrofuran-2(3H)-one as a colorless oil, which was carried as is in the next step.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiondiluted with water and benzophenone
  3. extractionwas extracted with diethyl ether (3×)
  4. extractionextracted with DCM (×2)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b6f8d85bea242548bed64faff1ae22a
Source dataset
uspto-grants-2010_10
Patent number
US07816378B2

Reaction notes

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