Ethyl Acetate → 2-Dimethylamino-4-(naphth-1-yl)oxazole

HRID 33562

Reaction equation

HRID 33562 reaction equation
Br[CH2:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=O.[CH3:15][N:16]([CH3:20])[C:17]([NH2:19])=[O:18].C(OCC)(=O)C>CN(C)C=O>[CH3:15][N:16]([CH3:20])[C:17]1[O:18][CH:2]=[C:3]([C:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7][CH:6]=2)[N:19]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11737N,N-DimethylureaHCID 38305132-Bromo-1-(1-naphthalenyl)ethanone

Product 1

HCID 597968722-Dimethylamino-4-(naphth-1-yl)oxazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(α-Bromoacetyl)naphthalene (5 g) and 1,1-dimethylurea (6 g) were stirred in anhydrous dimethylformamide (20 ml) at 105° C. overnight. The mixture was cooled, added to ethyl acetate, washed with sodium bicarbonate solution, water, brine, dried with sodium sulphate, filtered and evaporated in vacuo. The title compound was obtained (0.60 g; m.p. 30-32° C.) following silica gel column chromatography of the residue in dichloromethane.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with sodium bicarbonate solution, water, brine
  3. dry with materialdried with sodium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-31fee4816a474d2a8db741e1ab749da3
Source dataset
uspto-grants-2008_09
Patent number
US07429607B2

Linked notes

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