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

HRID 2121724Notes

Reaction equation

HRID 2121724 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-a53ef0327cc24e5c89d7ce8f26015a6f
Source dataset
uspto-grants-2004_02
Patent number
US06696470B2

Reaction notes

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