2-Aminothiazole → HCID 59733064, compound

HRID 1983228Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[C:7]([N:14]1[CH:18]=[CH:17]N=[CH:15]1)(N1C=CN=C1)=[O:8].CN[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][C:28]1C=C[CH:31]=[CH:30][CH:29]=1.C(OCC)(=O)C>ClC(Cl)C>[CH3:15][N:14]([C:18]1[CH:17]=[CH:31][CH:30]=[CH:29][C:28]=1[O:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:21]=1)[C:7]([NH:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1)=[O:8]

Participants

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-Methyl-2-phenoxyaniline (0.40 g, 2.00 mmol) was added to the solution. The reaction mixture was then stirred overnight at 80° C. The reaction was monitored by LC-MS and TLC, then concentrated under reduced pressure to afford crude product which subsequently was subjected to silica gel chromatography (hexanes:ethyl acetate from 80:20 to 50:50 as eluent system) to afford title product (0.48 g, 73%) as orange solid.

Workup

concentrationconcentrated under reduced pressure
customto afford crude product which

Sources & evidence

ORD record: ord-cfd8d357fe9046aaaaa9885b83e17c3a
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541373B2

Reaction notes

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