Diethylamine → N,N-diethylthiophene-3-carboxamide

HRID 2410242Notes

Reaction equation

HRID 2410242 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6](Cl)=[O:7])=[CH:2]1.[CH2:9]([NH:11][CH2:12][CH3:13])[CH3:10]>C(Cl)Cl>[CH2:9]([N:11]([CH2:12][CH3:13])[C:6]([C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)=[O:7])[CH3:10]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 27763773-Thenoyl chloride

Product 1

HCID 11389776N,N-diethylthiophene-3-carboxamideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thiophene-3-carbonyl chloride was dissolved in methylene chloride (100 mL) and added to a mixture of diethylamine (43.8 g, 0.6 mol) and methylene chloride (100 mL) placed in an ice bath. Following the addition, the ice bath was removed and the resulting reaction mixture stirred at room temperature over a period of 4 h. The reaction mixture was washed several times with water and the organic layer dried over anhydrous magnesium sulfate and concentrated. Vacuum distillation of the crude residue afforded the title compound as a light yellow oil (yield: 91%): GC-Ms: 183; 1H NMR (300 MHz, CDCl3, ppm) δ: 7.36(d, 1H), 7.22-7.19(m, 1H), 7.08-7.06(m, 1H).

Workup

  1. customplaced in an ice bath
  2. additionthe addition
  3. customthe ice bath was removed
  4. customthe resulting reaction mixture
  5. washThe reaction mixture was washed several times with water
  6. dry with materialthe organic layer dried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. distillationVacuum distillation of the crude residue

Sources & evidence

ORD record
ord-6e90c2b556fa42a282c9985c750d8959
Source dataset
uspto-grants-2014_08
Patent number
US08816035B2

Reaction notes

Loading…