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Ammonium Chloride → 2[2-(2-Methylphenoxymethyl)-benzoyl]-imidazole

HRID 567114
Notes
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Reaction equation

HRID 567114 reaction equation
C(OC(OCC)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)C.C([Li])CCC.[CH3:18][C:19]1[CH:39]=[CH:38][CH:37]=[CH:36][C:20]=1[O:21][CH2:22][C:23]1[CH:35]=[CH:34][CH:33]=[CH:32][C:24]=1[C:25](N1CCCC1)=[O:26].[Cl-].[NH4+]>O1CCCC1.CO>[CH3:18][C:19]1[CH:39]=[CH:38][CH:37]=[CH:36][C:20]=1[O:21][CH2:22][C:23]1[CH:35]=[CH:34][CH:33]=[CH:32][C:24]=1[C:25]([C:6]1[NH:5][CH:9]=[CH:8][N:7]=1)=[O:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 38495351-(diethoxymethyl)-1H-imidazoleHCID 21264588HCID 21264588, compoundHCID 178418339Butyllithium

Product 1

HCID 153461052[2-(2-Methylphenoxymethyl)-benzoyl]-imidazoleYield 63.9%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

At −40° C., 6.9 g (0.0405 mol) of N-diethoxymethylimidazole (J. Org. Chem. Vol. 45, No. 20, 1980, page 4040) in 40 ml of tetrahydrofuran are mixed with 11.3 g (0.0405 mol) of 23% pure n-butyllithium, and the mixture is stirred at −60° C. for one hour. At −40° C., 6 g (0.0203 mol) of N-[2-(2-methylphenoxymethyl)-benzoyl]-pyrrolidine are added, and the mixture is stirred for 30 minutes without any further cooling, on which the reaction mixture warms to 20° C. 5 g of ammonium chloride and 50 ml of methanol are added, and the mixture is heated at reflux for 15 minutes. The volatile components are distilled off under reduced pressure and the residue is admixed with water and extracted with ethyl acetate. The organic phase is dried and concentrated under reduced pressure. The residue is recrystallized from ethyl acetate. 3.79 g (63.8% of theory) of 2[2-(2-methylphenoxymethyl)-benzoyl]-imidazole are obtained.

Workup

  1. customAt −40° C.
  2. stirringthe mixture is stirred for 30 minutes without any further cooling, on which the reaction mixture
  3. customwarms to 20° C
  4. temperaturethe mixture is heated
  5. temperatureat reflux for 15 minutes
  6. distillationThe volatile components are distilled off under reduced pressure
  7. extractionextracted with ethyl acetate
  8. customThe organic phase is dried
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-bfb1cab7d81e4942a10ae14ffd0fdfd0
Source dataset
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06177459B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes