Sodium Hydroxide → 1-[3'-chloro-4'-(N,N-dimethylcarbamoyl)phenyl]-3,3-dimethylazetidin-2-one

HRID 359054Notes

Reaction equation

HRID 359054 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:14]=[C:13]([NH:15][C:16](=[O:22])[C:17]([CH3:21])([CH3:20])[CH2:18]Cl)[CH:12]=[CH:11][C:5]=1[C:6]([N:8]([CH3:10])[CH3:9])=[O:7]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(Cl)Cl>[Cl:3][C:4]1[CH:14]=[C:13]([N:15]2[CH2:18][C:17]([CH3:21])([CH3:20])[C:16]2=[O:22])[CH:12]=[CH:11][C:5]=1[C:6](=[O:7])[N:8]([CH3:10])[CH3:9]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 539806102-chloro-4-(3'-chloro-2',2'-dimethylpropionamido)-N,N-dimethylbenzamide

Product 1

HCID 191042781-[3'-chloro-4'-(N,N-dimethylcarbamoyl)phenyl]-3,3-dimethylazetidin-2-oneYield 58.3%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

A solution of sodium hydroxide (4.00 g) and tetrabutylammonium bromide (0.10 g) in water (10 ml) was added to a suspension of 2-chloro-4-(3'-chloro-2'2'-dimethylpropionamido)-N,N-dimethylbenzamide (1.00 g) in methylene chloride (10 ml) and the two-phase system stirred at room temperature for 1 hour. Water (10 ml) and methylene chloride (10 ml) were then added and the whole methylene chloride layer washed with brine, dried and evaporated to give a pale yellow solid. This was recrystallised from ethyl acetate/hexane to give 1-[3'-chloro-4'-(N,N-dimethylcarbamoyl) phenyl]-3,3-dimethylazetidin-2-one as a white crystalline solid (0.516 g), m.p. 122°-123° C.

Workup

  1. washthe whole methylene chloride layer washed with brine
  2. customdried
  3. customevaporated
  4. customto give a pale yellow solid
  5. customThis was recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-dffd278fd39a4ddf840653a0e02e6cf0
Source dataset
uspto-grants-1991_03
Patent number
US04999381

Reaction notes

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