Chloroacetyl chloride → 8-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 2175217Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2175217
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[OH:9].C(=O)(O)[O-].[Na+].Cl[CH2:16][C:17](Cl)=[O:18]>C(#N)C.O.CCOC(C)=O>[Br:8][C:4]1[C:3]2[O:9][CH2:16][C:17](=[O:18])[NH:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

Komponenten

7

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 155315062-Amino-6-bromophenol

Produkt 1

HCID 218735338-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-oneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-amino-6-bromophenol (1 g, 5.32 mmol) in acetonitrile (10 mL) and water (10 mL) was added sodium bicarbonate (1.028 g, 12.23 mmol). The mixture was cooled to 0° C. and chloroacetyl chloride (0.554 mL, 6.91 mmol) was added dropwise. The reaction was refluxed overnight. After cooling to room temperature, the mixture was diluted with EtOAc, washed with water, dried over anhydrous MgSO4, filtered, and concentrated to afford the title compound (1.14 g, 94% yield) as a dark brown solid. 1H NMR (400 MHz, CDCl3) δ 8.22 (br. s, 1H), 7.23 (dd, J=8.0, 1.4 Hz, 1H), 6.86 (t, J=8.0 Hz, 1H), 6.76 (dd, J=7.9, 1.3 Hz, 1H), 4.74 (s, 2H).

Aufarbeitung

  1. temperatureThe reaction was refluxed overnight
  2. temperatureAfter cooling to room temperature
  3. washwashed with water
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b3380e3769174ad9b564c6279e138203
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062028B2

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