Potassium Carbonate → N-(4-bromophenyl)-2-(4-ethyl-4-isopropyl-2,5-dioxoimidazolidin-1-yl)acetamide

HRID 1025533Notes

Reaction equation

HRID 1025533 reaction equation
[CH2:1]([C:3]1([CH:10]([CH3:12])[CH3:11])[NH:7][C:6](=[O:8])[NH:5][C:4]1=[O:9])[CH3:2].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:24])[CH2:22]Cl)=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:21](=[O:24])[CH2:22][N:5]2[C:4](=[O:9])[C:3]([CH2:1][CH3:2])([CH:10]([CH3:11])[CH3:12])[NH:7][C:6]2=[O:8])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 17374N-(4-Bromophenyl)-2-chloroacetamideHCID 2345135-Ethyl-5-(propan-2-yl)imidazolidine-2,4-dione

Product 1

HCID 71664632N-(4-bromophenyl)-2-(4-ethyl-4-isopropyl-2,5-dioxoimidazolidin-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-Ethyl-5-(1-methylethyl)-2,4-imidazolidinedione, (CAS #98492-91-2 (50 mg, 0.29 mmol), N-(4-bromophenyl)-2-chloro-acetamide (CAS #2564-02-5) (80 mg, 0.32 mmol), K2CO3 (48 mg, 0.35 mmol) in acetone was stirred at ambient temperature for 18 h. The mixture was extracted with EtOAc, the organic layer was washed with brine, dried over MgSO4, filtered and solvent removed. The crude product was purified by preparative TLC. The title compound was isolated as white solid.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customsolvent removed
  6. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-3440bad861ec4af0aaf44df09e30acfb
Source dataset
uspto-grants-2014_05
Patent number
US08729096B2

Reaction notes

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