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Sodium Iodide → 2-[4-(1H-Imidazol-1-yl)phenoxy]-N,N-bis(phenylmethyl)-ethanamine dihydrochloride

HRID 232318
Notes
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Reaction equation

HRID 232318 reaction equation
[H-].[Na+].[N:3]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH:7]=[CH:6][N:5]=[CH:4]1.[ClH:15].[Cl:16][CH2:17][CH2:18][N:19]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[I-].[Na+]>CN(C)C=O>[ClH:16].[ClH:15].[N:3]1([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:17][CH2:18][N:19]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:10][CH:9]=2)[CH:7]=[CH:6][N:5]=[CH:4]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 5925Dibenamine hydrochlorideHCID 24758Sodium hydrideHCID 823151-(p-Hydroxyphenyl)imidazole

Product 1

HCID 200313912-[4-(1H-Imidazol-1-yl)phenoxy]-N,N-bis(phenylmethyl)-ethanamine dihydrochloride

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a cold suspension of 33 g (0.82 mol) 50% sodium hydride in 500 mL dimethylformamide, add 50.4 g (0.315 mol) 4-(1H-imidazol-1-yl)phenol portionwise, maintaining the temp below 10° C. After addition, stir at room temp for 1 hr. Add 93.2 (0.315 mol) 2-chloro-N,N-dibenzylethanamine hydrochloride portionwise followed by 2.35 g (0.16 mol) sodium iodide. Heat the reaction to 50° C. for 24 hr. After this time, quench with 15 mL H2O, filter, and remove the solvents. Dissolve the residue in methanolic HCl and remove the solvents to provide the title compound which can be recrystallized from isopropanol.

Workup

  1. temperaturemaintaining the temp below 10° C
  2. additionAfter addition
  3. temperatureHeat
  4. customthe reaction to 50° C. for 24 hr
  5. customAfter this time, quench with 15 mL H2O
  6. filtrationfilter
  7. customremove the solvents
  8. dissolutionDissolve the residue in methanolic HCl
  9. customremove the solvents

Sources & evidence

ORD record
ord-8150034b83084e448806bd3b849b2fce
Source dataset
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04851526

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes