Acetyl chloride → N-[4-(2-methoxy-naphthalen-1-yl)-oxazol-2-yl]-acetamide

HRID 33570Notes

Reaction equation

HRID 33570 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:13]1[N:14]=[C:15]([NH2:18])[O:16][CH:17]=1.C(N(CC)CC)C.[C:26](Cl)(=[O:28])[CH3:27]>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:13]1[N:14]=[C:15]([NH:18][C:26](=[O:28])[CH3:27])[O:16][CH:17]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 44215764HCID 44215764, compound

Product 1

HCID 59796888N-[4-(2-methoxy-naphthalen-1-yl)-oxazol-2-yl]-acetamideYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-methoxy-naphthalen-1-yl)-oxazol-2-ylamine (17, 450 mg), triethylamine (0.78 mL) and dichloromethane (5 mL) at 0° C. was added acetyl chloride (0.2 mL). The solution was allowed to warm to room temperature overnight and the reaction was quenched by the addition of a mixture of dichloromethane and methanol. The solution was washed with brine (×2), dried over magnesium sulfate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography, eluting with 2% methanol in dichloromethane, to afford N-[4-(2-methoxy-naphthalen-1-yl)-oxazol-2-yl]-acetamide (25) (190 mg, 36%) as an off-white solid. 1H NMR (DMSO-D6): 2.1 (3H, br s), 3.9 (3H, s), 7.2 (1H, s), 7.35-7.40 (1H, m), 7.45-7.50 (1H, m), 7.55 (1H, d, J=9.2 Hz), 7.90-7.95 (2H, m), 8.05 (1H, d, J=9.2 Hz), 11.2 (1H, br s). Mass Spectrum (m/z): 283 (M+H)+.

Workup

  1. customthe reaction was quenched by the addition of a mixture of dichloromethane and methanol
  2. washThe solution was washed with brine (×2)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe residue was purified by column chromatography
  7. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-c4005c6ed79a49aea66f613f81e60f6b
Source dataset
uspto-grants-2008_09
Patent number
US07429607B2

Reaction notes

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