Hydrochloric Acid → HCID 131712307, compound

HRID 893967Notes

Reaction equation

HRID 893967 reaction equation
Br[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[N:6]=[C:5]([Cl:14])[CH:4]=1.[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[CH:23]([OH:30])[CH2:24][N:25]1[CH:29]=[CH:28][N:27]=[CH:26]1.[OH-].[Na+].Cl>O.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.C(OCC)(=O)C.CCOCC.O1CCCC1>[ClH:13].[Cl:14][C:5]1[CH:4]=[C:3]([CH2:2][O:30][CH:23]([C:17]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=2[Cl:15])[CH2:24][N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[N:6]=1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 32238(+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanolHCID 21162225HCID 21162225, compound

Product 1

HCID 131712307HCID 131712307, compound

Reagents, catalysts & solvents 5

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

8.7 g of 4-bromomethyl-2,6-dichloroquinoline (0.03 mol), 7.7 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.03 mol), 30 g of sodium hydroxide (0.75 mol) dissolved in 30 ml water, 0.5 g of benzyltrimethylammonium chloride and 100 ml of tetrahydrofuran are reacted as described in Example 1. Work up of the mixture results in an oil, which after treatment in boiling ether, is dissolved in 250 ml of ethyl acetate. To the charcoaled solution is added etheral hydrochloric acid. The precipitated hydrochloride is filtered off, washed with ethyl acetate, treated with boiling acetonitrile and finally with anhydrous ether. Yield 4.9 g (32.6%); m.p. 192°-194° C.

Workup

  1. customresults in an oil, which after treatment
  2. filtrationThe precipitated hydrochloride is filtered off
  3. washwashed with ethyl acetate
  4. additiontreated with boiling acetonitrile and finally with anhydrous ether

Sources & evidence

ORD record
ord-a793e6d674f143f7910f8dd1099abfa9
Source dataset
uspto-grants-1981_08
Patent number
US04282230

Reaction notes

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