Hydrochloric Acid → HCID 131712309, compound

HRID 893970Notes

Reaction equation

HRID 893970 reaction equation
Cl.[Cl:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[CH:22]([OH:29])[CH2:23][N:24]1[CH:28]=[CH:27][N:26]=[CH:25]1.[OH-].[Na+].Cl>O.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CCOCC.O1CCCC1>[ClH:2].[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[CH:22]([O:29][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH2:23][N:24]1[CH:28]=[CH:27][N:26]=[CH:25]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 32238(+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanolHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 131712309HCID 131712309, compound

Reagents, catalysts & solvents 4

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.2 g of 2-Chloromethylquinoline hydrochloride (0.015 mol) (commercially available), 3.85 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.015 mol), 14.8 g sodium hydroxide (0.37 mol) in 25 ml of water, 0.25 g of benzyltrimethylammonium chloride and 40 ml of tetrahydrofuran are reacted in a manner as described in Example 1. After work up, the oily product (6.4 g) is dissolved in 150 ml of ether, charcoaled and then etheral hydrochloric acid is added to the clear solution while stirring. The precipitated hydrochloride (5.8 g) is filtered off, washed with ether and hexane and recrystallized from acetonitrile; m.p. 148°-149° C.

Workup

  1. filtrationThe precipitated hydrochloride (5.8 g) is filtered off
  2. washwashed with ether and hexane
  3. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-3e7bbd4fcc034d7c8ca206bb28e01490
Source dataset
uspto-grants-1981_08
Patent number
US04282230

Reaction notes

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