Ammonium Chloride → 3-Chloro-4-[4-(2,4-dichlorobenzylidene)cyclohexyl]amino-2-ethylpyridine

HRID 1020

Reaction equation

HRID 1020 reaction equation
[Cl:1][C:2]1[C:3]([CH2:9][CH3:10])=[N:4][CH:5]=[CH:6][C:7]=1Cl.[Cl:11][C:12]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:13]=1[CH:14]=[C:15]1[CH2:20][CH2:19][CH:18]([NH2:21])[CH2:17][CH2:16]1.[Cl-].[NH4+].C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[Cl:1][C:2]1[C:3]([CH2:9][CH3:10])=[N:4][CH:5]=[CH:6][C:7]=1[NH:21][CH:18]1[CH2:17][CH2:16][C:15](=[CH:14][C:13]2[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:12]=2[Cl:11])[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 196940164-(2,4-Dichlorobenzylidene)cyclohexylamineHCID 217084253,4-Dichloro-2-ethylpyridine

Product 1

HCID 196940093-Chloro-4-[4-(2,4-dichlorobenzylidene)cyclohexyl]amino-2-ethylpyridineYield 7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1.6 g of 3,4-dichloro-2-ethylpyridine and 2.5 g of 4-(2,4-dichlorobenzylidene)cyclohexylamine are heated at 180° C. for 3.5 hours together with 55 g of ammonium chloride in 9 ml of N-methylpyrrolidone. After cooling, the mixture is poured into saturated sodium bicarbonate solution and extracted with ethyl acetate. The product is purified by chromatography on silica gel using ethyl acetate/heptane 1:4. Yield: 7%

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. customThe product is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c0062b7363ec4154b00b2b22681d2f1d
Source dataset
uspto-grants-1998_03
Patent number
US05723450

Linked notes

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