Triethylamine → 5-Carbamoyl-1H-imidazol-4-yl-1-adamantanecarboxylate

HRID 443583Notes

Reaction equation

HRID 443583 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.[C:17]12([C:27](Cl)=[O:28])[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[CH2:18]1)[CH2:24]2>CN(C)C=O>[C:17]12([C:27]([O:9][C:8]3[N:7]=[CH:6][NH:5][C:4]=3[C:1](=[O:3])[NH2:2])=[O:28])[CH2:24][CH:23]3[CH2:22][CH:21]([CH2:20][CH:19]([CH2:25]3)[CH2:18]1)[CH2:26]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 178513830HCID 178513830, compound

Product 1

HCID 644655-Carbamoyl-1H-imidazol-4-yl-1-adamantanecarboxylateYield 64.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 4-carbamoylimidazolium-5-olate (1.016 g) in dimethylformamide (20 ml) was added triethylamine (1.942 g) at 0°-5° C. and then 1-adamantanecarbonylchloride (3.50 g) in dimethylformamide (20 ml) dropwisely over 24 minutes. The reaction mixture was stirred at 0°-5° C. for 23 hours. The solvent was removed under reduced pressure. To the residue was added ethyl acetate (20 ml) and water (20 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 (1.5 g, α form, m.p. 206.5°-207.5° C. (dec.)), which was washed thoroughly with ethyl acetate to give pure product, α form, m.p. 211° C. (dec.).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionTo the residue was added ethyl acetate (20 ml) and water (20 ml)
  3. stirringstirred at room temperature for 1 hour
  4. filtrationThe insoluble solid was filtered
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-1b6bb6c01add4ce2a42ba07583835307
Source dataset
uspto-grants-1981_04
Patent number
US04260774

Reaction notes

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