Potassium Carbonate → 3,3-Dimethyl-1-[2-nitro-4-(trifluoromethyl)phenyl]azetidin-2-one

HRID 2115897Notes

Reaction equation

HRID 2115897 reaction equation
Cl[CH2:2][C:3]([CH3:21])([CH3:20])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18])=[O:5].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:2][C:3]1([CH3:21])[CH2:20][N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=2[N+:17]([O-:19])=[O:18])[C:4]1=[O:5]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 160861403-Chloro-2,2-dimethyl-N-[2-nitro-4-(trifluoromethyl)phenyl]propanamide

Product 1

HCID 269856283,3-Dimethyl-1-[2-nitro-4-(trifluoromethyl)phenyl]azetidin-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 3-chloro-2,2-dimethyl-N-(2-nitro-4-(trifluoromethyl)phenyl)propanamide (3.24 g, 10.0 mmol, 1.0 equiv) in acetone (100 mL) was added K2CO3 (3.5 g, 25.0 mmol, 2.5 equiv). was heated to 50° C. for 48 h. After filtering, the solvent was removed in vacuo and the resulting residue purified by silica gel chromatography (1:10 hexanes:EtOAc to 1:5 hexanes:EtOAc) to afford lactam 3. MS (MH+) 289.1; Calculated 289.1 for C12H12F3N2O3.

Workup

  1. filtrationAfter filtering
  2. customthe solvent was removed in vacuo
  3. customthe resulting residue purified by silica gel chromatography (1:10 hexanes:EtOAc to 1:5 hexanes:EtOAc)
  4. customto afford lactam 3

Sources & evidence

ORD record
ord-ca901efd54434c43ba7d48e2d3a0daaa
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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