Methylamine → n-Methyl-(2,5-dichlorothiophen-3-yl)carboxamide

HRID 1004175Notes

Reaction equation

HRID 1004175 reaction equation
[Cl:1][C:2]1[S:6][C:5]([Cl:7])=[CH:4][C:3]=1[C:8](Cl)=[O:9].[CH3:11][NH2:12]>C(Cl)Cl>[CH3:11][NH:12][C:8]([C:3]1[CH:4]=[C:5]([Cl:7])[S:6][C:2]=1[Cl:1])=[O:9]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 27770842,5-Dichlorothiophene-3-carbonyl chloride

Product 1

HCID 23434132n-Methyl-(2,5-dichlorothiophen-3-yl)carboxamideYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2,5-dichloro-3-thenoyl chloride (commercially available from Maybridge Chemical Co. Ltd. 1.07 g, 5 mM) in CH2Cl2 (5 mL) was added 40% aqueous solution of methylamine (1 mL) at room temperature. After stirring overnight, the mixture was poured into CH2Cl2 (50 mL). The whole was washed with water (40 mL), brine (40 mL), dried over MgSO4, and concentrated in vacuo. The resulting solid was triturated with Et2O-hexane to give the subtitle compound (0.54 g, 51% yield).

Workup

  1. washThe whole was washed with water (40 mL), brine (40 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting solid was triturated with Et2O-hexane

Sources & evidence

ORD record
ord-179a705b40474fd5a3f75b6658fc9395
Source dataset
uspto-grants-2000_04
Patent number
US06048880

Reaction notes

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