Acetic Anhydride → HCID 18630099, compound

HRID 1939010Notes

Reaction equation

HRID 1939010 reaction equation
[Cl:1][C:2]1[C:12]([CH:13]=O)=[CH:11][CH:10]=[C:9]([Si:15]([CH3:18])([CH3:17])[CH3:16])[C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5].Cl.[NH2:20]O.C(OC(=O)C)(=O)C>N1C=CC=CC=1>[Cl:1][C:2]1[C:12]([C:13]#[N:20])=[CH:11][CH:10]=[C:9]([Si:15]([CH3:18])([CH3:17])[CH3:16])[C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 443297Hydroxyamine hydrochlorideHCID 10660666HCID 10660666, compound

Product 1

HCID 18630099HCID 18630099, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A solution of the compound of Example 223 (0.28 g, 1.0 mmol) and hydroxylamine hydrochloride (0.12 g, 1.7 mmol) in pyridine (10 mL) was stirred at RT for 2 h. Acetic anhydride (0.75 mL, 8.0 mmol) was added and the solution was heated at 100° C. for 1.5 h. The mixture was concentrated, water added and the mixture extracted with ether. The organic layers were washed with 0.5N HCl, sat NaHCO3, brine, dried (MgSO4) and concentrated to afford the title compound. The crude product was purified by recrystallization from ethyl acetate/hexanes to afford 0.21 g of white needles (74%). m.p. 111°-112° C.

Workup

  1. concentrationThe mixture was concentrated
  2. additionwater added
  3. extractionthe mixture extracted with ether
  4. washThe organic layers were washed with 0.5N HCl
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1c254aa5b4a94153862636b1a800e49c
Source dataset
uspto-grants-1997_12
Patent number
US05693667

Reaction notes

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