Ethanol → 1-(4-Acetylaminophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 1904793Notes

Reaction equation

HRID 1904793 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]23[CH2:20][CH:19]2[C:18](=[O:21])[NH:17][C:16]3=[O:22])=[CH:11][CH:10]=1.CN(CCC)C.C(O)C>O1CCCC1>[C:1]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]23[CH2:20][CH:19]2[C:18](=[O:21])[NH:17][C:16]3=[O:22])=[CH:13][CH:14]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 7918Acetic AnhydrideHCID 61236N,N-DimethylpropylamineHCID 140689341-(4-Aminophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

Product 1

HCID 140689461-(4-Acetylaminophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.4 ml of acetic anhydride in 10 ml of tetrahydrofuran is added dropwise to a solution of 4 g of 1-(4-aminophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione and 120 mg of dimethylaminopropane in 150 ml of tetradrofuran, and the mixture is stirred overnight at room temperature. Then 0.5 ml of ethanol is added to the reaction mixture, which is stirred for 1 hour and filtered. The crystals so obtained are washed with tetrahydrofuran and ether, affording white crystals of the title compound with a melting point above 230° C. and Rf=0.3 in thin-layer silica gel plates in the system methylene chloride/methanol (10:1).

Workup

  1. stirringis stirred for 1 hour
  2. filtrationfiltered
  3. customThe crystals so obtained
  4. washare washed with tetrahydrofuran and ether

Sources & evidence

ORD record
ord-7b402f1f1e9547a4a06726842231205c
Source dataset
uspto-grants-1989_06
Patent number
US04839379

Reaction notes

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