Sulfuric Acid → HCID 57781091, compound

HRID 1690754Notes

Reaction equation

HRID 1690754 reaction equation
[OH:1][C:2]([CH3:18])([CH3:17])[CH:3]([C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[C:11]#N)[N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.S(=O)(=O)(O)[OH:20].C(=O)(O)[O-].[Na+]>O1CCOCC1.O>[N:4]1([CH:3]2[C:9]3[C:10](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:20])[O:1][C:2]2([CH3:18])[CH3:17])[CH:8]=[CH:7][N:6]=[CH:5]1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 57781131HCID 57781131, compound

Product 1

HCID 57781091HCID 57781091, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Crude 2-(2-hydroxy-1-imidazol-1-yl-2-methyl-propyl)-benzonitrile (1.75 g) is dissolved in dioxane (15 mL) and water (15 mL). Sulfuric acid (1.5 mL, 29.0 mmol) is added and the mixture is stirred at reflux for 2 h. After cooling down, the pH is adjusted with solid sodium bicarbonate. The mixture is extracted with ethyl acetate and the combined organic phase is washed with water, dried over Na2SO4 and concentrated in vacuo. The residue is purified by silica gel chromatography (dichloromethane-methanol, 19:1) to give 4-(imidazol-1-yl)-3,3-dimethyl-isochroman-1-one; MS (ESI) m/z 242.9 (M+H); 1H NMR (400 MHz, MeOD) δ ppm. 1.30 (s, 3 H), 1.53 (s, 3 H), 5.76 (s, 1 H), 6.98 (s, 1 H), 7.09 (s, 1 H), 7.52 (d, J=7.6 Hz, 1 H), 7.64-7.73 (m, 1 H), 7.76-7.85 (m, 1 H), 7.89 (s, 1 H), 8.25 (dd, J=7.7, 1.4 Hz, 1 H).

Workup

  1. temperatureat reflux for 2 h
  2. temperatureAfter cooling down
  3. extractionThe mixture is extracted with ethyl acetate
  4. washthe combined organic phase is washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography (dichloromethane-methanol, 19:1)

Sources & evidence

ORD record
ord-0e9b7687270c4aacb0f4803cd73fedb0
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

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