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

HRID 131780
ノート
印刷プレビュー

反応式

HRID 131780 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒

反応条件

温度
-30 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-65a2e44ac23245b9bc573b6972c82ac1
出典データセット
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07384967B2

反応ノート

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