Acetic Acid → HCID 178488970, compound

HRID 582141Notes

Reaction equation

HRID 582141 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3[NH:16][CH:17]=[C:18]([C:20](F)(F)F)[N:19]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[NH4+:25].C(O)(=O)C>CCOC(C)=O.CCCCCC>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3[NH:16][CH:17]=[C:18]([C:20]#[N:25])[N:19]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14923Ammonium HydroxideHCID 178488963HCID 178488963, compound

Product 1

HCID 178488970HCID 178488970, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 2-(3-cyclopentyloxy-4-methoxyphenyl)-4-trifluoromethyl-imidazole (1.04 g, 3.18 mmol) and 5% aqueous ammonium hydroxide (300 ml) was heated to reflux for 24 hours. The reaction mixture was cooled and carefully neutralised with acetic acid. The mixture was extracted with methylene chloride (3×150 ml) and the volatiles removed in vacuo to afford the crude product. Flash chromatography (SiO2 ; EtOAc:hexane (2:3)) produced the 2-(3-cyclopentyloxy-4-methoxyphenyl)-4-cyanoimidazole (320 mg, 35%) as a pale yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionThe mixture was extracted with methylene chloride (3×150 ml)
  5. customthe volatiles removed in vacuo
  6. customto afford the crude product

Sources & evidence

ORD record
ord-99cf3affa7944b9b93433603d43268f4
Source dataset
uspto-grants-1999_07
Patent number
US05922751

Reaction notes

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