Sodium Hydroxide → HCID 178516280, compound

HRID 893969Notes

Reaction equation

HRID 893969 reaction equation
Br[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([OH:13])[CH:4]=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+].[Na]>O.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O1CCCC1>[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[CH:22]([O:29][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([OH:13])[CH:4]=1)[CH2:23][N:24]1[CH:28]=[CH:27][N:26]=[CH:25]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 32238(+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanolHCID 5360545SodiumHCID 178515812HCID 178515812, compound

Product 1

HCID 178516280HCID 178516280, compound

Reagents, catalysts & solvents 3

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

7.2 g of 4-bromomethyl-2-hydroxyquinoline (0.03 mol), 7.7 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.03 mol), 30 g sodium hydroxide (0.75 mol) in 30 ml of water, 0.5 g benzyltrimethylammonium chloride and 45 ml of tetrahydrofuran are reacted in a manner as described in Example 1. After work up of the reaction mixture the sodium salt of the title compound is dissolved in 400 ml of water and acidified with acetic acid. After standing overnight, the solution is filtered and then neutralized with aqueous ammonia. The deposited oil is extracted with chloroform, the chloroform layer washed with water, dried with sodium sulfate and evaporated. The residual oil (8 g) is dissolved in 100 ml of ethyl acetate, charcoaled and allowed to stand overnight in the refrigerator. The crystallized 4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]-2-quinolinol melts at 190°-192° C.

Sources & evidence

ORD record
ord-1cadda93d72a42b4a8038c4bbbac59b9
Source dataset
uspto-grants-1981_08
Patent number
US04282230

Reaction notes

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