2-Aminothiazole → HCID 59732681, compound

HRID 131787Notes

Reaction equation

HRID 131787 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[C:7](N1C=CN=C1)(N1C=CN=C1)=[O:8].[CH:19]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([CH3:21])[CH3:20]>ClC(Cl)C>[CH:19]([N:22]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:7]([NH:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1)=[O:8])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 682631,1'-CarbonyldiimidazoleHCID 28545108N-isopropyl-2-phenoxyaniline

Product 1

HCID 59732681HCID 59732681, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-aminothiazole (0.20 g, 2.00 mmol) in dichloroethane (20 ml) was added 1,1′-carbonyldiimidazole (0.40 g, 2.5 mmol) and N,N-dimethylaminopyridine (0.05 g, 0.4 mmol) then the solution was refluxed at 80° C. for 1 h. N-Isopropyl-2-phenoxyaniline (0.46 g, 2.0 mmol) was added and the reaction mixture was then stirred overnight at 80° C. 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 50:50 as eluent system) to afford title product (0.56 g, 79%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto afford crude product, which
  3. customwas purified by silica gel chromatography (hexanes:ethyl acetate from 80:20 to 50:50 as eluent system)

Sources & evidence

ORD record
ord-69371012a4a94337aead069e3f9f4a95
Source dataset
uspto-grants-2008_06
Patent number
US07384967B2

Reaction notes

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