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

HRID 443584Notes

Reaction equation

HRID 443584 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 55.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1-adamantanecarbonylchloride (2.980 g) in pyridine (26 ml) was added 4-carbamoylimidazolium-5-olate (1.271 g) and the reaction temperature was kept at 40°-43° C. for 4 hours. Unreacted starting material was recovered by filtration (210 mg). The filtrate was concentrated under reduced pressure. To the residue was added ethyl acetate (30 ml) and water (30 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 (1.602 g, α form, m.p. 207°-209° C. (dec.)).

Workup

  1. filtrationwas recovered by filtration (210 mg)
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. additionTo the residue was added ethyl acetate (30 ml) and water (30 ml)
  4. filtrationThe insoluble solid was filtered
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-14894b972b7e4c06a7f63795408aaceb
Source dataset
uspto-grants-1981_04
Patent number
US04260774

Reaction notes

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