Sodium Carbonate → 6-(2,4-Dichlorophenyl)imidazo[1,2-a]pyrazin-8(7H)-one

HRID 444811Notes

Reaction equation

HRID 444811 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[C:12]1[C:16]([O:18]CC)=O.C([O-])(=O)C.[NH4+:26].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:26][C:16](=[O:18])[C:12]2[N:11]([CH:15]=[CH:14][N:13]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 517165Ammonium AcetateHCID 58170070Ethyl 1-[2-(2,4-dichlorophenyl)-2-oxoethyl]-1H-imidazole-2-carboxylate

Product 1

HCID 581699896-(2,4-Dichlorophenyl)imidazo[1,2-a]pyrazin-8(7H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

920 mg (2.8 mmol) of ethyl 1-[2-(2,4-dichlorophenyl)-2-oxoethyl]-1H-imidazol-2-carboxylate (Example 3A) were dissolved in 45 ml of glacial acetic acid, and 2.17 g (28 mmol) of ammonium acetate were added. The mixture was stirred under reflux for 12 h. The reaction mixture was added to ice-water and neutralized and with sodium carbonate. The precipitate was filtered off and dried under high vacuum. This gave 650 mg (82% of theory) of the product as a solid.

Workup

  1. temperatureunder reflux for 12 h
  2. filtrationThe precipitate was filtered off
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-d82aeb24a5a34ae5b894032844ef6d02
Source dataset
uspto-grants-2013_07
Patent number
US08476267B2

Reaction notes

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