Sodium Bicarbonate → 1-Carboxy-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol

HRID 728332Notes

Reaction equation

HRID 728332 reaction equation
C([CH2:3][C:4]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])([OH:11])[CH2:5][N:6]1[CH:10]=[N:9][CH:8]=[N:7]1)#N.[C:20](=[O:23])(O)[O-:21].[Na+]>S(=O)(=O)(O)O.O>[C:20]([CH2:3][C:4]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])([OH:11])[CH2:5][N:6]1[CH:10]=[N:9][CH:8]=[N:7]1)([OH:21])=[O:23]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 133903931-Cyano-2-(2,4-Dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)-2-propanol

Product 1

HCID 198241601-Carboxy-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

1-Cyano-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)-2-propanol (4 g, 13.9 mmole) was dissolved in 40% aqueous sulfuric acid (100 ml) and heated in an oil bath at 100°-110° C. for 18 hours. The solution was then cooled, diluted with water (200 ml), and rendered alkaline by the slow addition of solid sodium bicarbonate. The mixture was then extracted several times with ethyl acetate (3×100 ml) and the aqueous phase was rendered acidic (pH 3) by the addition of dilute orthophosphoric acid. The aqueous phase was then extracted with ethyl ether (3×150 ml), the combined ether extracts were washed once with water, and then dried over magnesium sulfate. Evaporation of the ether gave the title compound as a pale yellow solid, 2.7 g, (62%), m.p. 158°-159° C.

Workup

  1. temperatureheated in an oil bath at 100°-110° C. for 18 hours
  2. temperatureThe solution was then cooled
  3. extractionThe mixture was then extracted several times with ethyl acetate (3×100 ml)
  4. additionby the addition of dilute orthophosphoric acid
  5. extractionThe aqueous phase was then extracted with ethyl ether (3×150 ml)
  6. washthe combined ether extracts were washed once with water
  7. dry with materialdried over magnesium sulfate
  8. customEvaporation of the ether

Sources & evidence

ORD record
ord-a072a926c88e41ea923830aac872a45b
Source dataset
uspto-grants-1991_09
Patent number
US05047548

Reaction notes

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