Methylamine → n-Methyl-2-methylthiophene-3-carboxamide
Reaction equation
[Cl-].[CH3:2][C:3]1[S:4][CH:5]=[CH:6][C:7]=1[C:8]([O-:10])=O.C1COCC1.[CH3:16][NH2:17]>C(OCC)(=O)C>[CH3:16][NH:17][C:8]([C:7]1[CH:6]=[CH:5][S:4][C:3]=1[CH3:2])=[O:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Methyl-3-thiophenecarboxylate chloride (60.5 g)/THF (300 ml) solution was added dropwise to a 40% aqueous solution of methylamine (400 ml) at 0° C. Ethyl acetate (21) was added thereto, and then the organic layer was washed sequentially with water, a 5N aqueous solution of hydrochloric acid, an aqueous solution of saturated sodium bicarbonate, water and brine, dried and evaporated. The resulting residue was crystallized from n-hexane, to give the title compound as awhite powder (43.5 g, yield; 71.8%).
Workup
- washthe organic layer was washed sequentially with water
- dry with materiala 5N aqueous solution of hydrochloric acid, an aqueous solution of saturated sodium bicarbonate, water and brine, dried
- customevaporated
- customThe resulting residue was crystallized from n-hexane
Sources & evidence
- ORD record
- ord-723685352bb448ed8a221db4fb6e8ddd
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06790844B2
Reaction notes
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