HCID 21833844, compound → HCID 21833760, compound

HRID 1741067Notes

Reaction equation

HRID 1741067 reaction equation
O1CCO[CH:2]1[CH:6](C)[CH2:7][NH:8][C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[C:12]([CH3:17])[CH:11]=1>O>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]2[O:18][C:6]([CH3:2])=[CH:7][N:8]=2)=[CH:11][C:12]=1[CH3:17]

Participants

3

Reactant 1

HCID 21833844HCID 21833844, compound

Product 1

HCID 21833760HCID 21833760, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

N-[2-(1,3-Dioxolan-2-yl)propyl]-4-bromo-3-methylbenzamide (D74, 2.8 g, 8.9 mmole) was added portionwise over 5 minutes to well stirred polyphosphoric acid (50 g) at 120° C. under argon, then heated at 160° C. for 35 minutes. The reaction mixture was allowed to cool, then treated with water (200 ml) and stirred well to dissolve the glassy mass. The mixture was extracted with ethyl acetate and the extract washed with 10% Na2CO3 solution and water, then dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 1:1 ether/60-80 petrol to afford the title compound as a pale yellow solid (2.0 g, 89%).

Workup

  1. temperatureto cool
  2. dissolutionto dissolve the glassy mass
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract washed with 10% Na2CO3 solution and water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with 1:1 ether/60-80 petrol

Sources & evidence

ORD record
ord-b825061e1096456dbbda54f9f8fe9051
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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