Ethylene Glycol → HCID 58244020, compound

HRID 389129Notes

Reaction equation

HRID 389129 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][C:14]1([C:17]2[N:21]([CH3:22])[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]([F:32])([F:31])[F:30])=[N:19][N:18]=2)[CH2:16][CH2:15]1)[C:7](N)=[O:8].C(O)C[OH:35]>O>[Br:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][C:14]1([C:17]2[N:21]([CH3:22])[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]([F:30])([F:31])[F:32])=[N:19][N:18]=2)[CH2:15][CH2:16]1)[C:7]([OH:8])=[O:35]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 58243848HCID 58243848, compound

Product 1

HCID 58244020HCID 58244020, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

Potassium hydroxide (87 mg) was added to a mixture of 3-bromo-4-[(1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}cyclopropyl)oxy]benzamide (250 mg) and ethyleneglycol (6 ml), followed by stirring at 130° C. for 3 hours. The reaction solution was cooled to room temperature, and water was added thereto, followed by washing with ethyl acetate. The aqueous layer was acidified with 1M hydrochloric acid and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting product was solidified with diisopropylether and washed to obtain, as a colorless solid, 3-bromo-4-[(1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}cyclopropyl)oxy]benzoic acid (71 mg).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. washby washing with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washwashed

Sources & evidence

ORD record
ord-e9e0fc26b4bb480a8838d3a43c2deacb
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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