Hydrochloric Acid → HCID 131710633, compound

HRID 435871Notes

Reaction equation

HRID 435871 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.[H-].[Na+].[N+:16]([C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][Cl:22])([O-:18])=[O:17].Cl>CO.CCOCC>[ClH:22].[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:21][C:20]2[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=2[N+:16]([O-:18])=[O:17])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 119212-Nitrobenzyl chlorideHCID 24758Sodium hydrideHCID 13621746HCID 13621746, compound

Product 1

HCID 131710633HCID 131710633, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

Analogously to Example 1, a crude ether is obtained from 1.74 g. of 4-(1-imidazolylmethyl)-phenol, 300 mg. of sodium hydride suspension, and 1.72 g. of 2-nitrobenzyl chloride. This crude ether is dissolved in methanol and combined with an excess of methanol which contains hydrogen chloride until the mixture shows an acidic reaction. After the solvent has been removed by evaporation under vacuum, the residue is dissolved in methylene chloride and mixed with ether until the onset of crystallization, thus obtaining 925 mg. of [4-(1-imidazolylmethyl)-phenyl]-(2-nitrobenzyl)-ether, hydrochloride, which melts at 156°-158° after another recrystallization from isopropanol.

Workup

  1. customan acidic reaction
  2. customAfter the solvent has been removed by evaporation under vacuum
  3. dissolutionthe residue is dissolved in methylene chloride
  4. additionmixed with ether until the onset of crystallization
  5. customthus obtaining 925 mg
  6. customof [4-(1-imidazolylmethyl)-phenyl]-(2-nitrobenzyl)-ether, hydrochloride, which melts at 156°-158° after another recrystallization from isopropanol

Sources & evidence

ORD record
ord-1570f52d15614f2f96264b846395c417
Source dataset
uspto-grants-1977_02
Patent number
US04006243

Reaction notes

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