Triethylamine → HCID 66653417, compound

HRID 1035167Notes

Reaction equation

HRID 1035167 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:20](=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][NH:9][C:20](=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 77174p-Toluohydrazide

Product 1

HCID 66653417HCID 66653417, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Methylbenzohydrazide (6 g, 40 mmol) was dissolved in DCM (100 mL) and triethylamine (7.3 g, 80 mmol) was added. The solution was cooled with an ice-bath and ethyl chloro(oxo)acetate (5.5 g, 40 mmol) was added dropwise. After completed addition the reaction was stirred at 0° C. for 1 h and at rt for 2 h. The reaction mixture was washed with 0.2 M HCl, aqueous NaHCO3 solution (sat.) and brine. The organic solution was filtered through a phase separator and the solvent was removed by evaporation. There was obtained 8.1 g (81%) of 6A as a white solid. 1H NMR (400 MHz, CDCl3): δ 1.36 (t, 3H), 2.38 (s, 3H), 4.35 (q, 2H) 7.21 (d, 2H), 7.73 (d, 2H).

Workup

  1. temperatureThe solution was cooled with an ice-bath
  2. additionaddition the reaction
  3. washThe reaction mixture was washed with 0.2 M HCl, aqueous NaHCO3 solution (sat.) and brine
  4. filtrationThe organic solution was filtered through a phase separator
  5. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-46cf61d4084a42e69eb9f016c030693b
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

Loading…