2-Chloro-N,N-dimethylethylamine → HCID 70089870, compound

HRID 359480Notes

Reaction equation

HRID 359480 reaction equation
[C:1]([C:11]1[C:12]([O:17][C:18]2[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[CH:20][C:19]=2[OH:26])=[N:13][CH:14]=[CH:15][CH:16]=1)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:33][N:34]([CH3:38])[CH2:35][CH2:36]Cl>CN(C)C=O>[ClH:24].[C:1]([C:11]1[C:12]([O:17][C:18]2[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[CH:20][C:19]=2[O:26][CH2:36][CH2:35][N:34]([CH3:38])[CH3:33])=[N:13][CH:14]=[CH:15][CH:16]=1)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 11430Potassium CarbonateHCID 54524372HCID 54524372, compound

Product 1

HCID 70089870HCID 70089870, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 20 ml of dimethylformamide are added 7.7 g of 3-cinnamoyl- 2-(4,5-dichloro-2-hydroxyphenoxy)pyridine and 3.3 g of potassium carbonate, and the mixture is stirred at room temperature for 30 minutes Thereto, 2.8 g of 2-dimethylaminoethyl chloride is added, and the mixture is stirred at 50° C. for 6 hours. The reaction mixture is poured into ice-water, followed by extraction with toluene After the extract is washed with water and dried over anhydrous magnesium sulfate, the solvent is distilled off. The residue is converted into its hydrochloride in isopropyl alcohol and the hydrochloride is recrystallized from isopropyl alcohol to give 3-cinnamoyl-2-[4,5-dichloro-2-(2-dimethylaminoethoxy)phenoxy]pyridine hydrochloride, m.p. 169°-171° C.

Workup

  1. stirringthe mixture is stirred at 50° C. for 6 hours
  2. extractionfollowed by extraction with toluene After the extract
  3. washis washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off
  6. customthe hydrochloride is recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-272d8f3cced74ecbb4f757f8a7b03aae
Source dataset
uspto-grants-1991_03
Patent number
US05001137

Reaction notes

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