Sulfuric Acid → HCID 11965455, compound

HRID 906529Notes

Reaction equation

HRID 906529 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([CH:10]2[CH2:14][CH2:13][CH2:12][O: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]([CH:10]2[CH2:14][CH2:13][CH2:12][O:11]2)[C:7]([C:15]([F:17])([F:18])[F:16])=[CH:6][C:5]=1[NH2:19]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 585329182-Acetylamino-5-(tetrahydro-furan-2-yl)-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 11965455HCID 11965455, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-acetylamino-5-(tetrahydro-furan-2-yl)-4-trifluoromethyl-benzoic acid methyl ester (8.25 g, 24.9 mmol) in MeOH (100 mL) and water (10 mL) was cooled to 0° C. Concd H2SO4 (6.88 mL, 125 mmol) was added dropwise. The solution was refluxed for 45 min, cooled to r.t., diluted with ice/water and extracted with EtOAc. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 1:4 EtOAc/hexanes) to give the title product (5.06 g, 68%) as colorless crystals. m.p.: 131-136° C., API-ES: m/z 290 [M+H]+.

Workup

  1. temperatureThe solution was refluxed for 45 min
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (silica gel, 1:4 EtOAc/hexanes)

Sources & evidence

ORD record
ord-a9e7cd5b114541ceb9b79b3960b09f38
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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