Sulfuric Acid → HCID 58964479, compound

HRID 2069264Notes

Reaction equation

HRID 2069264 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[N:13][N:12]=[CH:11]2)[C:7]([C:15]([F:18])([F:17])[F:16])=[CH:6][C:5]=1[NH:19]C(=O)C.OS(O)(=O)=O>CO.O>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([N:10]2[CH:11]=[N:12][N:13]=[CH:14]2)[C:7]([C:15]([F:18])([F:16])[F:17])=[CH:6][C:5]=1[NH2:19]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 58964480HCID 58964480, compound

Product 1

HCID 58964479HCID 58964479, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 450 mg (1.43 mmol) of 2-acetylamino-5-[1,2,4]triazol-4-yl-4-trifluoromethyl-benzoic acid methyl ester in 5 ml methanol and 1 ml water is cooled to 0° C. and treated dropwise with 0.6 ml (11.3 mmol) of concentrated H2SO4. The mixture is then heated to reflux for 30 minutes and allowed to cool to room temperature. It is poured onto ice and the resulting mixture extracted with ethyl acetate. The organic phase is dried over Na2SO4, filtered and concentrated in vacuo. The crude product is recrystallized in ethyl acetate/hexane to give 292 mg (71%) of 2-amino-5-[1,2,4]triazol-4-yl-4-trifluoromethyl-benzoic acid methyl ester, m.p. 184-186° C.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureto reflux for 30 minutes
  3. additionIt is poured onto ice
  4. extractionthe resulting mixture extracted with ethyl acetate
  5. dry with materialThe organic phase is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is recrystallized in ethyl acetate/hexane

Sources & evidence

ORD record
ord-83f1b2765e0648cfbc2c99626429151e
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

Loading…