Ethylamine → Thiophenecarboxamide,N-ethyl-

HRID 1939019Notes

Reaction equation

HRID 1939019 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[CH2:9]([NH2:11])[CH3:10]>C(Cl)Cl.O>[CH2:9]([NH:11][C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[O:7])[CH3:10]

Participants

5

Reactant 2

HCID 6341EthylamineHCID 789282-Thiophenecarbonyl chloride

Product 1

HCID 5151566Thiophenecarboxamide,N-ethyl-Yield 83.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-thiophenecarboxylic acid chloride (7.3 g, 50 mmol) in 30 mL CH2Cl2 was added to 70% ethylamine in water (11 g) at -5° C. and the resulting solution was stirred at RT for 18 h. After that, water was added. The organic layer was separated, washed with water, brine, dried and concentrated. Purification of the residue by flash chromatography with 25% ethyl acetate-hexane gave 6.4 g (83.1% yield) of N-ethyl-2-thiophenecarboxamide as a white solid, m.p. 75°-78° C.

Workup

  1. customThe organic layer was separated
  2. washwashed with water, brine
  3. customdried
  4. concentrationconcentrated
  5. customPurification of the residue by flash chromatography with 25% ethyl acetate-hexane

Sources & evidence

ORD record
ord-f09a0579b7614256ab184ffae95b0d38
Source dataset
uspto-grants-1997_12
Patent number
US05693667

Reaction notes

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