Potassium Hydroxide → HCID 58497952, compound

HRID 1505236Notes

Reaction equation

HRID 1505236 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][C:13]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)([C:15]([F:18])([F:17])[F:16])N=N2)=[CH:6][C:5]=1[CH3:27].[OH-].[K+]>CO.O>[Cl:25][C:23]1[CH:24]=[C:19]([C:13]2([C:15]([F:18])([F:17])[F:16])[CH2:14][N:10]2[C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:28])=[C:5]([CH3:27])[CH:6]=2)[CH:20]=[C:21]([Cl:26])[CH:22]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67218075HCID 67218075, compound

Product 1

HCID 58497952HCID 58497952, compoundYield 36.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-[1,2,3]triazol-1-yl]-2-methyl-benzoic acid methyl ester (Example 2.1) (3.6 g, 8.33 mmol) in methanol (10 ml) was added aqueous potassium hydroxide (40% w/v) (35 ml) and the reaction mixture heated at 80° C. for 15 hours. The reaction mixture was then diluted with water and extracted with ethyl acetate. The aqueous phase was acidified by addition of aqueous hydrochloric acid (1M) and extracted again with ethyl acetate (3×200 ml). The combined organic extracts were washed with brine and concentrated. The residue was purified by column chromatography on silica gel (eluent: 15% v/v ethyl acetate in hexane) to give 4-[2-(3,5-dichloro-phenyl)-2-trifluoromethyl-aziridin-1-yl]-2-methyl-benzoic acid as a white solid (1.2 g). 1H-NMR (DMSO-d6, 400 MHz): 12.57 (s, 1H), 7.70 (d, 1H), 7.65 (s, 3H), 6.99 (s, 1H), 6.97 (d, 1H), 3.27 (s, 1H), 3.05 (s, 1H), 2.45 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. additionThe aqueous phase was acidified by addition of aqueous hydrochloric acid (1M)
  3. extractionextracted again with ethyl acetate (3×200 ml)
  4. washThe combined organic extracts were washed with brine
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (eluent: 15% v/v ethyl acetate in hexane)

Sources & evidence

ORD record
ord-38f7fb83b9fa481785013fc7034961eb
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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