1-Adamantanecarbonyl chloride → 5-Carbamoyl-1H-imidazol-4-yl-1-adamantanecarboxylate

HRID 443582Notes

Reaction equation

HRID 443582 reaction equation
[C:1]12([C:11](Cl)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:14]([C:17]1[NH:18][CH:19]=[NH+:20][C:21]=1[O-:22])(=[O:16])[NH2:15]>N1C=CC=CC=1>[C:1]12([C:11]([O:22][C:21]3[N:20]=[CH:19][NH:18][C:17]=3[C:14](=[O:16])[NH2:15])=[O:12])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

4

Reactant 2

HCID 989151-Adamantanecarbonyl chlorideHCID 178513830HCID 178513830, compound

Product 1

HCID 644655-Carbamoyl-1H-imidazol-4-yl-1-adamantanecarboxylateYield 89.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1-adamantanecarbonylchloride (39.73 g) in pyridine (260 ml) was added 4-carbamoylimidazolium-5-olate (12.71 g) and the reaction temperature was maintained at 41°-43° C. for 3.5 hours. Pyridine was removed under reduced pressure. To the residue was added ethylacetate (300 ml) and water (300 ml), and stirred at room temperature for 1 hour. The insoluble solid was filtered and washed with ethyl acetate to give almost pure 5-carbamoyl-1H-imidazol-4-yl 1-adamantanecarboxylate (25.9 g, β form, m.p. 205°-205.5° C. (dec.)). Recrystallization from dimethylformamide-diethylether gave analytically pure sample (β form m.p. 213.5°-216.5° C. (dec.)).

Workup

  1. temperaturethe reaction temperature was maintained at 41°-43° C. for 3.5 hours
  2. customPyridine was removed under reduced pressure
  3. additionTo the residue was added ethylacetate (300 ml) and water (300 ml)
  4. filtrationThe insoluble solid was filtered
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-5cc8250a900648ffa1d4560d1c91b848
Source dataset
uspto-grants-1981_04
Patent number
US04260774

Reaction notes

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