Acetyl chloride → HCID 19779538, compound

HRID 2082095Notes

Reaction equation

HRID 2082095 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:12][CH:11]([NH:13][OH:14])[CH2:10]2)[CH:6]=[CH:7][CH:8]=1.C[O:16][C:17]1C=C(C=C[CH:24]=1)C=O.FC1C=C[C:29]([O:30]C2C=C(C=CC=2)C=O)=[CH:28]C=1.C(Cl)(=O)C>C(Cl)Cl.C(N(CC)CC)C>[C:17]([O:14][N:13]([CH:11]1[CH2:10][CH:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:12]1)[C:29](=[O:30])[CH3:28])(=[O:16])[CH3:24]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 115693-MethoxybenzaldehydeHCID 3085320Benzaldehyde, 3-(4-fluorophenoxy)-HCID 19779536HCID 19779536, compound

Product 1

HCID 19779538HCID 19779538, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3-(3-methoxyphenyl)cyclobutylhydroxylamine (34.8 mmol), prepared according to the procedure described in Example 1 substituting 3-methoxybenzaldehyde for 3-(4-fluorophenoxy)benzaldehyde, in CH2Cl2 (150 mL) at 0° C., was added acetyl chloride (8.20 g, 104.4 mmol) followed by the dropwise addition of triethylamine and a few crystals of N,N-dimethylaminopyridine. The cooling bath was withdrawn and the reaction allowed to warm to ambient temperature. It was then diluted with brine (100 mL) and the layers were separated. The aqueous phase was extracted with CH2Cl2 (2×100 mL). The organics were combined, dried over MgSO4 and concentrated to afford crude N-acetoxy-N-[3-(3-methoxyphenyl)cyclobutyl]-acetamide.

Workup

  1. customThe cooling bath was withdrawn
  2. additionIt was then diluted with brine (100 mL)
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted with CH2Cl2 (2×100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-799fddf8be884b748eb3397b7b4ce449
Source dataset
uspto-grants-1993_02
Patent number
US05187192

Reaction notes

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