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

HRID 2276080

Reaction equation

HRID 2276080 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-28cbd86608134804891b3b422a69f60b
Source dataset
uspto-grants-2015_09
Patent number
USRE045670E1

Linked notes

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