Ethanol → HCID 20339483, compound

HRID 1395521Notes

Reaction equation

HRID 1395521 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[CH:3]=1.[H-].[Na+].Cl.[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19]Cl.C(O)C>CN(C)C=O.O>[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19][N:9]([C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]=1)[C:10](=[O:12])[CH3:11]

Participants

7

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 223262N-(4,6-Dimethylpyridin-2-yl)ethanimidic acidHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 20339483HCID 20339483, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

One hundred and seventy seven grams (1.08 moles) of N-(4,6-dimethyl-2-pyridyl)acetamide is dissolved in 1.8 l of dry dimethylformamide in a 3 liter 3-neck flask equipped with a mechanical stirrer, thermometer, drying tube and slow nitrogen sweep. Sodium hydride in mineral oil (57%, 45.5 g) is added over a 30 minute period. After stirring for an additional 15 minutes, one hundred thirteen grams of 2-dimethylaminoethyl chloride hydrochloride is added in three portions over a 30 minute period. This is followed by 25.7 g of sodium hydride added in portions over a 60 minute period. Then 58.7 g of 2-dimethylaminoethyl chloride hydrochloride is added over a few minute period followed by 25.7 g of sodium hydride. A total of 96.9 g (2.3 mole) of 57% sodium hydride in mineral oil and 171.7 g (1.2 mole) of 2-dimethylaminoethyl chloride hydrochloride are used. The reaction mixture is stirred at 50° for 30 minutes then heated at 95° for 21/2 hours. After adding 75 ml of ethanol and 75 ml of water, the dimethylformamide is removed by distillation in vacuum.

Workup

  1. customequipped with a mechanical stirrer
  2. customthermometer, drying tube
  3. additionSodium hydride in mineral oil (57%, 45.5 g) is added over a 30 minute period
  4. additionone hundred thirteen grams of 2-dimethylaminoethyl chloride hydrochloride is added in three portions over a 30 minute period
  5. additionadded in portions over a 60 minute period
  6. additionThen 58.7 g of 2-dimethylaminoethyl chloride hydrochloride is added over a few minute period
  7. stirringThe reaction mixture is stirred at 50° for 30 minutes
  8. temperaturethen heated at 95° for 21/2 hours
  9. customthe dimethylformamide is removed by distillation in vacuum

Sources & evidence

ORD record
ord-f2af48fc5d2f4ed5833920fd0d38f24e
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

Loading…