Acetic Anhydride → HCID 18630099, compound

HRID 2394891Notes

Reaction equation

HRID 2394891 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 0.5 N 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 0.5 N HCl
  5. customdried (MgSo4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-482cbf2bf86c46edba6ec84abf1ef691
Source dataset
uspto-grants-1998_09
Patent number
US05811411

Reaction notes

Loading…