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

HRID 443582노트

반응식

HRID 443582 반응식
[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

참가 물질

4

반응물 2

HCID 989151-Adamantanecarbonyl chlorideHCID 178513830HCID 178513830, 화합물

생성물 1

HCID 644655-carbamoyl-1H-imidazol-4-yl-1-adamantanecarboxylate수율 89.5%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.)).

후처리

  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

출처 및 근거

ORD 기록
ord-5cc8250a900648ffa1d4560d1c91b848
출처 데이터셋
uspto-grants-1981_04
특허 번호
US04260774

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