Water → HCID 58902391, compound

HRID 1640137Notes

Reaction equation

HRID 1640137 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:12](O)([CH3:14])[CH3:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.S(=O)(=O)(O)O.O.C([O-])([O-])=[O:23].[Na+].[Na+].[C:28](#[N:30])[CH3:29]>>[NH2:1][C:2]1[CH:3]=[C:4]([C:12]([NH:30][C:28](=[O:23])[CH3:29])([CH3:14])[CH3:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

6

Reactant 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 58902253HCID 58902253, compound

Product 1

HCID 58902391HCID 58902391, compoundYield 44%

Procedure

To a solution of 2-[3-amino-5-(trifluoromethyl)phenyl]propan-2-ol (2.05 g, 9.35 mmol) in acetonitrile (110 mL), was added concentrated sulfuric acid (1.99 mL, 37.4 mol).The reaction was allowed to stir at rt for 72 h. Water was added and the pH was adjusted to 8 by the addition of saturated aq. Na2CO3. The mixture was extracted with EtOAc (2×) and the combined organic solutions were washed with water then brine, dried over Na2SO4, filtered and evaporated. The residue was triturated with DCM and the solid was collected. The filtrate was evaporated and further purified by column chromatography. The solid and column fractions were combined to give N-{1-[3-amino-5-(trifluoromethyl)phenyl]-1-methylethyl}acetamide (1.07 g, 44.0%). LCMS: (FA) ES+ 261.1.

Workup

  1. extractionThe mixture was extracted with EtOAc (2×)
  2. washthe combined organic solutions were washed with water
  3. dry with materialbrine, dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was triturated with DCM
  7. customthe solid was collected
  8. customThe filtrate was evaporated
  9. customfurther purified by column chromatography

Sources & evidence

ORD record
ord-70a4e6efd350473ea27fd10aedf20736
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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