2-Aminothiazole → 1-(2-Phenoxyphenyl)-5-(thiazol-2-yl)biuret

HRID 598912

반응식

HRID 598912 반응식
[O:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:24](=[O:29])=[N:25][C:26](Cl)=[O:27].[NH2:30][C:31]1[S:32][CH:33]=[CH:34][N:35]=1>O1CCCC1>[O:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH:10][C:24]([NH:25][C:26]([NH:30][C:31]1[S:32][CH:33]=[CH:34][N:35]=1)=[O:27])=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 21552-AminothiazoleHCID 75899Benzenamine, 2-phenoxy-HCID 81531DiisopropylethylamineHCID 119708Isocyanatocarbonyl chloride

생성물 1

HCID 597330351-(2-Phenoxyphenyl)-5-(thiazol-2-yl)biuret수율 55.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-30 °C

실험 절차

To a solution of 2-phenoxyaniline (0.46 g, 2.50 mmol) in tetrahydrofuran (20 ml) was added diisopropylethylamine (0.89 ml, 5.00 mmol) and the solution was cooled to −30° C., then N-(chlorocarbonyl)isocyanate (0.3 ml, 3.75 mmol) was slowly added. The mixture was then allowed to warm up to the room temperature during 30 min. 2-Aminothiazole (0.375 g, 3.75 mmol) was added to the reaction mixture and stirred at room temperature for 6 hours. The reaction mixture was concentrated under reduced pressure to afford crude product, which was purified by silica gel chromatography (hexanes:ethyl acetate from 80:20 to 30:70) to afford title compound (0.49 g, 55%) as pale yellow solid.

후처리

  1. temperatureto warm up to the room temperature during 30 min
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto afford crude product, which
  4. customwas purified by silica gel chromatography (hexanes:ethyl acetate from 80:20 to 30:70)

출처 및 근거

ORD 기록
ord-3dac87a570b6488e8231d9879114e80b
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897628B2

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