1,1'-Carbonyldiimidazole → Brofoxine

HRID 50661

Reaktionsgleichung

Reaktionsgleichung von HRID 50661
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([OH:12])([CH3:11])[CH3:10].[C:13](N1C=CN=C1)(N1C=CN=C1)=[O:14]>C1COCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:13](=[O:14])[O:12][C:9]([CH3:10])([CH3:11])[C:3]=2[CH:4]=1

Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 120422752-(2-Amino-5-bromophenyl)propan-2-ol

Produkt 1

HCID 30630Brofoxine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 2-(2-amino-5-bromophenyl)propan-2-ol (18 g, 78 mmol) in dry THF (150 mL) was added 1,1′-carbonyldiimidazole (15.5 g, 94 mmol) under nitrogen. The reaction solution was heated at 50° C. overnight. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate (100 mL). The solution was washed with 1N aqueous hydrochloride solution (2×40 mL), brine (20 mL), and dried with MgSO4. After removal of solvent in vacuo, 6-bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one was obtained as a white solid (20 g, 100%): mp 199-200° C.; 1H-NMR (DMSO-d6) δ 10.32 (s, 1H, D2O exchangeable), 7.48 (d, 1H, J=2.1 Hz), 7.43 (dd, 1H, J=8.5, 2.1 Hz), 6.84 (d, 1H, J=8.4 Hz), 1.61 (s, 6H).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  3. washThe solution was washed with 1N aqueous hydrochloride solution (2×40 mL), brine (20 mL)
  4. dry with materialdried with MgSO4
  5. customAfter removal of solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e3ee2b37c40040f9a9f7f26480c44eb1
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713478B2

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