Ammonium Acetate → HCID 58248787, compound

HRID 2040398Notes

Reaction equation

HRID 2040398 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]([C:27](=O)[CH2:28][CH2:29][CH2:30][CH3:31])[CH2:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23]C(=O)C)=[CH:19][CH:18]=3)=O)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:39]>C(O)(=O)C>[CH2:28]([C:27]1[N:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][C:5]3[CH:33]=[CH:34][C:2]([Cl:1])=[CH:3][CH:4]=3)=[CH:8][CH:9]=2)[CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[N:39]=1)[CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 66919878HCID 66919878, compound

Product 1

HCID 58248787HCID 58248787, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of acetic acid 4-(2-{[4-(4-chloro-phenoxy)-phenyl]-pentanoyl-amino}-acetyl)-phenyl ester (from above, based on 200 mmol) with ammonium acetate (308 g, 4000 mmol, 20.0 eq) in acetic acid (300 mL) was stirred at 100-110° C. overnight. After completion of the reaction (indicated by HPLC), the mixture was cooled below 60° C. and poured over ice. After stirring, the solid was filtered, washed with diethyl ether (twice), ethyl acetate (twice), ether (once) and air dried, yielding ˜55.0 g (65.6%) of 4-{2-butyl-1-[4-(4-chloro-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenol as a finely divided off-white solid.

Workup

  1. customAfter completion of the reaction (indicated by HPLC)
  2. temperaturethe mixture was cooled below 60° C.
  3. additionpoured over ice
  4. stirringAfter stirring
  5. filtrationthe solid was filtered
  6. washwashed with diethyl ether (twice), ethyl acetate (twice), ether (once) and air
  7. customdried

Sources & evidence

ORD record
ord-b4e4952f4072486aa4895a81d2768cd4
Source dataset
uspto-grants-2013_11
Patent number
US08580833B2

Reaction notes

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