Diethyl Ether → HCID 178520539, compound

HRID 744039Notes

Reaction equation

HRID 744039 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][C:16]#N)[N:10]=[CH:9]2)C=CC=CC=1.[C:30]1([CH2:36][CH2:37][CH2:38][Mg]Br)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[Cl-].[NH4+].C([O:45]CC)C>O1CCCC1>[NH:8]1[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][C:16](=[O:45])[CH2:38][CH2:37][CH2:36][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:10]=[CH:9]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 11474387HCID 11474387, compoundHCID 178418471HCID 178418471, compound

Product 1

HCID 178520539HCID 178520539, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5 mmol of 4-(1-(triphenylmethyl)imidazol-4-yl)butanenitrile are introduced into a solution of 3-phenylpropylmagnesium bromide in 300 ml of diethyl ether and 100 ml of tetrahydrofuran and the mixture is brought to reflux for 6 h. Hydrolysis is carried out with an ammonium chloride solution, the organic phase is separated and the aqueous phase is stirred with dichloromethane. The combined and concentrated organic phases are brought to boiling point for 2 h in a 2N aqueous/alcohol (ethanol/water) hydrochloric acid solution. The ethanol is removed under vacuum, filtration is carried out and basification is carried out. The title compound is stirred in dichloromethane and recrystallized in the hydrogenmaleate form from ethanol/diethyl ether.

Workup

  1. temperatureto reflux for 6 h
  2. customHydrolysis
  3. customthe organic phase is separated
  4. customfor 2 h
  5. customThe ethanol is removed under vacuum, filtration
  6. stirringThe title compound is stirred in dichloromethane
  7. customrecrystallized in the hydrogenmaleate form from ethanol/diethyl ether

Sources & evidence

ORD record
ord-558dad95af7248079e9209386a495763
Source dataset
uspto-grants-1996_09
Patent number
US05559113

Reaction notes

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