Methanol → 2-Acetylamino-4-(naphth-1-yl)oxazole

HRID 33563Notes

Reaction equation

HRID 33563 reaction equation
[NH2:1][C:2]1[O:3][CH:4]=[C:5]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][CH:8]=2)[N:6]=1.C(N(CC)CC)C.[C:24](Cl)(=[O:26])[CH3:25].CO>ClCCl>[C:24]([NH:1][C:2]1[O:3][CH:4]=[C:5]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][CH:8]=2)[N:6]=1)(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 103079572-Amino-4-(naphth-1-yl)oxazole

Product 1

HCID 597968402-Acetylamino-4-(naphth-1-yl)oxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (ice/salt bath) mixture of 2-amino-4-(naphth-1-yl)oxazole (1)(0.5 g) and triethylamine (0.8 ml) in anhydrous dichloromethane (5 ml) was added dropwise acetyl chloride (0.2 ml) over a minute. The resulting mixture was warmed to room temperature and left overnight. Further acetyl chloride (0.1 ml) was added and the mixture left for a further hour. Dichloromethane (40 ml) and few drops of methanol were added. The mixture was washed twice with brine, dried with sodium sulphate, filtered and evaporated in vacuo. The title compound (9) (0.35 g; m.p. 188-190° C.) was obtained following silica gel column chromatography of the residue in 2% methanol in chloroform.

Workup

  1. temperatureTo a cooled
  2. waitthe mixture left for a further hour
  3. washThe mixture was washed twice with brine
  4. dry with materialdried with sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-4a542a07cdbf48b783167e4decab0fd8
Source dataset
uspto-grants-2008_09
Patent number
US07429607B2

Reaction notes

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