Sulfuric Acid → HCID 19956952, compound

HRID 2211089Notes

Reaction equation

HRID 2211089 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)([CH2:12][CH3:13])[C:9](N)=[O:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:21]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)([CH2:12][CH3:13])[C:9]([OH:21])=[O:10])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 199569554-Chlorophenyl-2-[(1,2,4-triazol-1-yl)methyl]butyramide

Product 1

HCID 19956952HCID 19956952, compound

Conditions

Temperature
10 °C

Procedure

To a 500 mL flask was charged 95 g (0.34 mole) of 2-(4-chlorophenyl-2-[(1,2,4-triazol-1-yl)methyl]butyramide and 95 g (0.97 mole) of 95% sulfuric acid and 95 g of ice. The reaction was stirred at reflux for 55 hours, after which the reaction was cooled to 10° C. and partitioned between ethyl acetate and water. The mixture was treated with 200 g of 10% sodium hydroxide which resulted in a pH 10 aqueous phase. The organic phase was extracted with 200 g of water, then 200 g of 10% sodium hydroxide and again with 200 mL of water The aqueous phases were combined and washed with ethyl ether then acidified to pH 5 at which point a solid formed. The solid was filtered, washed with water, dried and gave 73 g (77% yield) of a white solid, melting point 182°-184° C.

Workup

  1. temperatureat reflux for 55 hours
  2. custompartitioned between ethyl acetate and water
  3. additionThe mixture was treated with 200 g of 10% sodium hydroxide which

Sources & evidence

ORD record
ord-563c318317b345daad38e30bfbe6c2df
Source dataset
uspto-grants-1995_10
Patent number
US05462931

Reaction notes

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