Formaldehyde → N-{5-[(dimethylamino)methyl]-4-[(Z)-2-(4-nitrophenyl)vinyl]-1,3-thiazol-2-yl)acetamide
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]\[C:12]2[N:13]=[C:14]([NH:17][C:18](=[O:20])[CH3:19])[S:15][CH:16]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[CH3:22][NH:23][CH3:24].[CH2:25]=O>C(O)(=O)C>[CH3:22][N:23]([CH2:25][C:16]1[S:15][C:14]([NH:17][C:18](=[O:20])[CH3:19])=[N:13][C:12]=1/[CH:11]=[CH:10]\[C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:24]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of N-{4-[(Z)-2-(4-nitrophenyl)vinyl]-1,3-thiazol-2-yl}acetamide (500 mg) in acetic acid (3 ml) were added dimethylamine hydrochloride (169 mg) and paraformaldehyde (62.2 mg), and the mixture was stirred at 100° C. (bath temp.) for 2 hrs. The solvent was removed in vacuo, and the mixture was adjusted to pH=9 with saturated sodium hydrogen carbonate aqueous solution, extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. The crude compound was purified by flash column chromatography over silica gel with dichloromethane/methanol (100:1)→(20:1) as an eluent to give N-{5-[(dimethylamino)methyl]-4-[(Z)-2-(4-nitrophenyl)vinyl]-1,3-thiazol-2-yl}acetamide as a yellow amorphous substance.
Workup
- customThe solvent was removed in vacuo
- extractionextracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over magnesium sulfate
- customevaporated
- customThe crude compound was purified by flash column chromatography over silica gel with dichloromethane/methanol (100:1)→(20:1) as an eluent
Sources & evidence
- ORD record
- ord-0645b614014a40f289297e4357149acb
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07442715B2
Reaction notes
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