Water → 2-Chloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline

HRID 893966Notes

Reaction equation

HRID 893966 reaction equation
[OH-].[Na+].O.[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[CH:12]([OH:19])[CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.[Cl:20][C:21]1[CH:30]=[C:29]([CH2:31]Cl)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O1CCCC1>[Cl:20][C:21]1[CH:30]=[C:29]([CH2:31][O:19][CH:12]([C:6]2[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:5]=2[Cl:4])[CH2:13][N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 32238(+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanolHCID 12421948HCID 12421948, compound

Product 1

HCID 129533292-Chloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

In a three necked flask, fitted with stirrer, reflux condenser and gas inlet tube are introduced 30 g of sodium hydroxide (0.75 mol) and 30 ml of water. While passing nitrogen through the flask, the solution is cooled to 45° C. and then are added 7.7 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.03 mol), 0.5 g of benzyltrimethylammonium chloride, 100 ml of tetrahydrofuran and 6.4 g of 2-chloro-4-chloromethylquinoline (0.03 mol). Then the mixture is stirred vigorously for 1.5 hours at 60°-65° C. After cooling the mixture is separated, and the lower aqueous sodium hydroxide is extracted with 20 ml of tetrahydrofuran. The combined tetrahydrofuran layers are dried with sodium sulfate, charcoaled, filtered and after the solvent has been removed, the residual oil is extracted with 175 ml of ether, and the etheral solution is allowed to stand overnight in a refrigerator. The crystallized 2-chloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline is recrystallized from ethyl acetate (refrigerator). Yield 5.5 g (42.3%); m.p. 180°-181° C.

Workup

  1. customIn a three necked flask, fitted with stirrer
  2. temperaturereflux condenser and gas inlet tube
  3. temperatureAfter cooling the mixture
  4. customis separated
  5. extractionthe lower aqueous sodium hydroxide is extracted with 20 ml of tetrahydrofuran
  6. dry with materialThe combined tetrahydrofuran layers are dried with sodium sulfate
  7. filtrationfiltered
  8. customafter the solvent has been removed
  9. extractionthe residual oil is extracted with 175 ml of ether
  10. waitto stand overnight in a refrigerator
  11. customThe crystallized 2-chloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline is recrystallized from ethyl acetate (refrigerator)

Sources & evidence

ORD record
ord-0d9aa99a9e4a445eac65e9758149608f
Source dataset
uspto-grants-1981_08
Patent number
US04282230

Reaction notes

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