Methylamine → n-Methyl-2-methylthiophene-3-carboxamide

HRID 1006948Notes

Reaction equation

HRID 1006948 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

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 225034702-Methyl-3-thiophenecarboxylate chloride

Product 1

HCID 22503091n-Methyl-2-methylthiophene-3-carboxamideYield 71.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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

  1. washthe organic layer was washed sequentially with water
  2. dry with materiala 5N aqueous solution of hydrochloric acid, an aqueous solution of saturated sodium bicarbonate, water and brine, dried
  3. customevaporated
  4. 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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