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

HRID 131780

Reaction equation

HRID 131780 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-65a2e44ac23245b9bc573b6972c82ac1
Source dataset
uspto-grants-2008_06
Patent number
US07384967B2

Linked notes

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