Sulfuric Acid → HCID 178424567, compound

HRID 1926272Notes

Reaction equation

HRID 1926272 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:8]=1[CH2:9][NH:10][C:11](=[O:17])[CH:12](OC)OC.[OH-].[Na+]>>[CH3:22][C:19]1[CH:20]=[CH:21][C:7]([CH3:6])=[C:8]2[C:18]=1[CH:12]=[C:11]([OH:17])[N:10]=[CH:9]2

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 67520986HCID 67520986, compound

Product 1

HCID 178424567HCID 178424567, compound

Procedure

Sulfuric acid (18 M; 3.8 mL, 68 mmol) was added to N-(2,5-dimethylbenzyl)-2,2-dimethoxyacetamide (1.17 g, 4.92 mmol) at rt, and the solution was stirred at rt overnight. The solution was poured into ice, basified with NaOH (10 N) until pH>13, extracted with Et2O (3×30 ml), and the extracts were back-extracted with water (20 ml). The aqueous layer was neutralized with HCl until pH=7-8 and extracted with EtOAc (3×30 ml). The EtOAc extracts were washed with water (2×20 ml), brine (20 ml), dried over MgSO4, filtered, and concentrated in vacuo to give a brown solid. It was purified by prep. TLC eluting with 4% MeOH in DCM to give the title compound as yellow solid. 1H NMR (400 MHz, CDCl3): δ=2.46 (s, 3H), 2.55 (s, 3H), 6.84 (d, J=7.6 Hz, 1H), 6.98 (s, 1H), 7.16 (d, J=7.2 Hz, 1H), 8.61 (s, 1H). MS(ES+): m/z=173.43 (100) [MH+]. HPLC: tR=2.35 min (polar—5 min, ZQ3).

Workup

  1. additionThe solution was poured into ice
  2. extractionextracted with Et2O (3×30 ml)
  3. extractionthe extracts were back-extracted with water (20 ml)
  4. extractionextracted with EtOAc (3×30 ml)
  5. washThe EtOAc extracts were washed with water (2×20 ml), brine (20 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a brown solid
  10. customIt was purified by prep
  11. washTLC eluting with 4% MeOH in DCM

Sources & evidence

ORD record
ord-97a13658b25f460a875df3c3d4e06470
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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