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

HRID 443584ノート

反応式

HRID 443584 の反応式
[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

参加物

4

反応物 2

HCID 989151-Adamantanecarbonyl chlorideHCID 178513830HCID 178513830、化合物

生成物 1

HCID 644655-carbamoyl-1H-imidazol-4-yl-1-adamantanecarboxylate収率 55.4%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.)).

後処理

  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

出典と根拠

ORDレコード
ord-14894b972b7e4c06a7f63795408aaceb
出典データセット
uspto-grants-1981_04
特許番号
US04260774

反応ノート

読み込み中…