Water → HCID 131711751, compound

HRID 1395283Notes

Reaction equation

HRID 1395283 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[CH2:21][C:22]1[CH:23]=[N:24][C:25]2[C:30]([C:31]=1[Cl:32])=[CH:29][C:28]([Cl:33])=[CH:27][CH:26]=2>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O1CCCC1>[ClH:4].[Cl:32][C:31]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([Cl:33])[CH:29]=2)[N:24]=[CH:23][C:22]=1[CH2:21][O:19][CH:12]([C:6]1[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:5]=1[Cl:4])[CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 32238(+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanolHCID 20340826HCID 20340826, compound

Product 1

HCID 131711751HCID 131711751, compound

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

In a three necked flask, fitted with stirrer, reflux condenser and gas inlet tube are introduced 14.8 g. of sodium hydroxide (0.37 mol.) and 25 ml. of water. While passing nitrogen through the flask, the solution is cooled to 45° and then are added 3.85 g. of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.015 mol.), [prepared according to J. Med. Chem., Vol. 12, 784 (1969)], 0.25 g. of benzyltrimethylammonium chloride and 25 ml. of tetrahydrofuran. To the mixture, which is warmed to 50°, a solution of 3.6 g. of 3-chloromethyl-4,6-dichloroquinoline (0.015 mol.) in 10 ml. of tetrahydrofuran is added from a prewarmed dropping funnel within 3 minutes. The mixture is stirred vigorously for 3 hours at 60° using a water bath. Then the warm mixture is transferred into a separating funnel, the lower aqueous sodium hydroxide is extracted with 10 ml. of tetrahydrofuran. The combined tetrahydrofuran layers are dried by means of sodium sulfate, and after the solvent has been removed, the residual oil is extracted with ether, treated with charcoal and filtered. To the solution of free base are added dropwise ethereal hydrochloric acid. The precipitated 4,6-dichloro-3-[[1-(2,4-dichlorophenyl-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline, hydrochloride is filtered off, dried in the vacuum desiccator and recrystallized from absolute ethanol; yield: 1.9 g. (25%); m.p. 148°-150°.

Workup

  1. customIn a three necked flask, fitted with stirrer
  2. temperaturereflux condenser and gas inlet tube
  3. additionare introduced 14.8 g
  4. temperaturethe solution is cooled to 45°
  5. additionare added 3.85 g
  6. temperatureTo the mixture, which is warmed to 50°
  7. customwithin 3 minutes
  8. customThen the warm mixture is transferred into a separating funnel
  9. extractionthe lower aqueous sodium hydroxide is extracted with 10 ml
  10. dry with materialThe combined tetrahydrofuran layers are dried by means of sodium sulfate
  11. customafter the solvent has been removed
  12. extractionthe residual oil is extracted with ether
  13. additiontreated with charcoal
  14. filtrationfiltered
  15. additionTo the solution of free base are added dropwise ethereal hydrochloric acid
  16. filtrationThe precipitated 4,6-dichloro-3-[[1-(2,4-dichlorophenyl-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline, hydrochloride is filtered off
  17. customdried in the vacuum desiccator
  18. customrecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-8e1b3699e5d148e1a39fc2977a574da5
Source dataset
uspto-grants-1980_05
Patent number
US04202985

Reaction notes

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