Sulfuric Acid → HCID 178515346, compound

HRID 1926270Notes

Reaction equation

HRID 1926270 reaction equation
S(=O)(=O)(O)O.CO[CH:8](OC)[C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)=[O:10].[OH-].[Na+]>>[F:20][C:19]([F:22])([F:21])[C:16]1[CH:15]=[C:14]2[C:13](=[CH:18][CH:17]=1)[CH:12]=[N:11][C:9]([OH:10])=[CH:8]2

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 67520598HCID 67520598, compound

Product 1

HCID 178515346HCID 178515346, compound

Conditions

Temperature
50 °C

Procedure

Sulfuric acid (18 M; 2.25 mL, 40.5 mmol) was added to 2,2-dimethoxy-N-(4-trifluoromethylbenzyl)-acetamide (828 mg, 2.96 mmol) at rt. The combined solution was stirred at 50° C. overnight. The mixture was poured into ice, basified with NaOH (10 N) until pH>12, and extracted with EtOAc (3×50 ml). The extracts were washed with water (20 ml), dried over MgSO4, filtered, and concentrated in vacuo. The residue was triturated with 50% EtOAc/hexane (10 ml) to yield a yellow solid that was then purified by Gilson HPLC to give the title compound as yellow solid. 1H NMR (400 MHz, CDCl3): δ=7.18 (s, 1H), 7.45-7.51 (m, 1H), 7.96-8.02 (m, 2H), 8.89 (brs, 1H). MS(ES+): m/z=214.32 (100) [MH+]. HPLC: tR=2.64 min (polar—5 min, ZQ3).

Workup

  1. additionThe mixture was poured into ice
  2. extractionextracted with EtOAc (3×50 ml)
  3. washThe extracts were washed with water (20 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with 50% EtOAc/hexane (10 ml)
  8. customto yield a yellow solid
  9. customthat was then purified by Gilson HPLC

Sources & evidence

ORD record
ord-0619b5e359ec49939703445e6b4d3d31
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

Loading…