Triethylamine → HCID 53717583, compound

HRID 443580Notes

Reaction equation

HRID 443580 reaction equation
[C:1]([C:4]1[NH:5][CH:6]=[NH+:7][C:8]=1[O-:9])(=[O:3])[NH2:2].C(N(CC)CC)C.[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1>CN(C)C=O>[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([O:9][C:8]2[N:7]=[CH:6][NH:5][C:4]=2[C:1](=[O:3])[NH2:2])=[O:23])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 178513830HCID 178513830, compound

Product 1

HCID 53717583HCID 53717583, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 508 mg of 4-carbamoylimidazolium-5-olate and 486 mg of triethylamine in 6 ml of anhydrous dimethylformamide was added 770 mg of p-chlorobenzoyl chloride in 3 ml of anhydrous dimethylformamide at a temperature below 5° C. The mixture was stirred under ice cooling for 4 hours. The insoluble crystals were filtered off, then the filtrate were concentrated to a residue under reduced pressure, and the resulting residue was dissolved in chloroform. The chloroform solution was washed with water, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 5-carbamoyl-1H-imidazol-4-yl p-chlorobenzoate. The crude solid was washed with ethyl acetate to give 340 mg of pure product, m.p. 220° C. (charred).

Workup

  1. filtrationThe insoluble crystals were filtered off
  2. concentrationthe filtrate were concentrated to a residue under reduced pressure
  3. dissolutionthe resulting residue was dissolved in chloroform
  4. washThe chloroform solution was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f7b7d1bc559f41539eaa31f8fb2d1b00
Source dataset
uspto-grants-1981_04
Patent number
US04260774

Reaction notes

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