Water → 3-(2-Bromopropanoyl)spiro[benzo[e][1,3]oxazine-2,1'-cyclohexan]-4(3H)-one

HRID 1457363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1457363
[Br:1][CH:2]([CH3:6])[C:3](Br)=[O:4].N1C=CC=CC=1.[C:13]12([NH:23][C:22](=[O:24])[C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[O:19]1)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2.O>C(Cl)Cl>[Br:1][CH:2]([CH3:6])[C:3]([N:23]1[C:13]2([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[O:19][C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[C:22]1=[O:24])=[O:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 79047Propanoyl bromide, 2-bromo-HCID 652743spiro[benzo[e][1,3]oxazine-2,1'-cyclohexan]-4(3H)-one

Produkt 1

HCID 103380523-(2-Bromopropanoyl)spiro[benzo[e][1,3]oxazine-2,1'-cyclohexan]-4(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A solution of 89.1 ml of 2-bromopropionyl bromide in 95 ml of methylene chloride and a solution of 61.13 g of pyridine in 95 ml of methylene chloride are added dropwise to a suspension of 140 g of spiro[2,3-dihydro-4H-1,3-benzoxazine-2,1'-cyclohexan]-4-one in 190 ml of methylene chloride under nitrogen atmosphere at -5° C. during about 45 minutes. Then the mixture is stirred at a room temperature for 6 hours. The reaction mixture is poured into 500 ml of water and the mixture is extracted with methylene chloride. The extract is washed, dried and evaporated to remove the solvent and the residue obtained is crystallized from methanol and the crystals are collected by filtration to obtain 197.3 g of 3-(2-bromopropionyl)-spiro[2,3-dihydro-4H-1,3-benzoxazine-2,1'-cyclohexan]-4-one.

Aufarbeitung

  1. extractionthe mixture is extracted with methylene chloride
  2. washThe extract is washed
  3. customdried
  4. customevaporated
  5. customto remove the solvent
  6. customthe residue obtained
  7. customis crystallized from methanol
  8. filtrationthe crystals are collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-37c4039c7465403c8b81d4b3d0260745
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05847115

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