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

HRID 443582ノート

反応式

HRID 443582 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 89.5%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.)).

後処理

  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

出典と根拠

ORDレコード
ord-5cc8250a900648ffa1d4560d1c91b848
出典データセット
uspto-grants-1981_04
特許番号
US04260774

反応ノート

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