Sulfuric Acid → HCID 178515337, compound

HRID 1926271Notes

Reaction equation

HRID 1926271 reaction equation
S(=O)(=O)(O)O.CO[CH:8](OC)[C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([F:22])([F:21])[F:20])=[O:10].[OH-].[Na+]>>[F:20][C:19]([F:22])([F:21])[C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[CH:12]=[N:11][C:9]([OH:10])=[CH:8]2

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 675215012,2-Dimethoxy-N-[[2-(trifluoromethyl)phenyl]methyl]acetamide

Product 1

HCID 178515337HCID 178515337, compound

Conditions

Temperature
40 °C

Procedure

Sulfuric acid (18 M; 3.57 mL, 65.6 mmol) was added to 2,2-dimethoxy-N-(2-trifluoromethylbenzyl)-acetamide (1.33 g, 4.69 mmol) at rt. The solution was stirred at 40° C. overnight. The mixture was poured into ice, basified with NaOH (10 N) until pH>13, extracted with Et2O (3×30 ml), and the extracts were back-washed with water (20 ml). The combined aqueous layers were neutralized with HCl until pH=7-8 and extracted with EtOAc (3×30 ml). The EtOAc extract was washed with water (2×20 ml), brine (20 ml), dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as yellow solid. The material was used in the next step without further purification; a small quantity (15 mg) was purified using the Gilson HPLC for characterization by NMR. 1H NMR (400 MHz, DMSO-d6): δ=7.13 (s, 1H), 7.70 (t, 1H, J=8.0 Hz), 7.78 (d, 1H, J=7.2 Hz), 8.06 (d, 1H, J=8.4 Hz), 9.03 (t, 1H, J=1.0 Hz), 11.23 (brs, 1H). MS(ES+): m/z=213.38 (82) [MH+]. HPLC: tR=2.55 min (polar—5 min, ZQ3).

Workup

  1. additionThe mixture was poured into ice
  2. extractionextracted with Et2O (3×30 ml)
  3. washthe extracts were back-washed with water (20 ml)
  4. extractionextracted with EtOAc (3×30 ml)
  5. extractionThe EtOAc extract
  6. washwas washed with water (2×20 ml), brine (20 ml)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ed36871c68b4178892dbf18e1dc175e
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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