Chloroacetyl chloride → 1-(2-Chloro-acetyl)-3-(3-chloro-2-methyl-phenyl)-imidazolidin-4-one

HRID 1710673Notes

Reaction equation

HRID 1710673 reaction equation
C(O)(=O)C.[Cl:5][C:6]1[C:7]([CH3:18])=[C:8]([N:12]2[C:16](=[O:17])[CH2:15][NH:14][CH2:13]2)[CH:9]=[CH:10][CH:11]=1.C([O-])([O-])=O.[K+].[K+].[Cl:25][CH2:26][C:27](Cl)=[O:28]>C(Cl)Cl.O>[Cl:25][CH2:26][C:27]([N:14]1[CH2:15][C:16](=[O:17])[N:12]([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([Cl:5])[C:7]=2[CH3:18])[CH2:13]1)=[O:28]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 684655543-(3-Chloro-2-methyl-phenyl)-imidazolidin-4-one acetic acid salt

Product 1

HCID 594340271-(2-Chloro-acetyl)-3-(3-chloro-2-methyl-phenyl)-imidazolidin-4-one

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

To a mixture of 3-(3-chloro-2-methyl-phenyl)-imidazolidin-4-one acetic acid salt (75) (422 mg, 1 equiv) and K2CO3 (552 mg) in 5 mL of DCM/water (1:1 v/v) was added chloroacetyl chloride (240 μL, 1.5 equiv). One hour later, the organic layer was separated and dried over sodium sulfate to give 1-(2-chloro-acetyl)-3-(3-chloro-2-methyl-phenyl)-imidazolidin-4-one (76).

Workup

  1. customOne hour later, the organic layer was separated
  2. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-7f8d692e69474af9af342b86f7f3834d
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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