3-Bromo-o-toluidine → 2-amino-N-(3-bromo-2-methylphenyl)-3-chlorobenzamide

HRID 523211

Reaktionsgleichung

Reaktionsgleichung von HRID 523211
[Cl:1][C:2]1[C:7]2[NH:8]C(=O)[O:10][C:11](=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:14][C:15]1[C:16]([CH3:22])=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18]>C1(C)C(C)=CC=CC=1>[NH2:8][C:7]1[C:2]([Cl:1])=[CH:3][CH:4]=[CH:5][C:6]=1[C:11]([NH:18][C:17]1[CH:19]=[CH:20][CH:21]=[C:15]([Br:14])[C:16]=1[CH3:22])=[O:10]

Komponenten

4

Edukt 2

HCID 1235383-Bromo-o-toluidineHCID 5175353-Chloroisatoic anhydride

Produkt 1

HCID 1076239932-amino-N-(3-bromo-2-methylphenyl)-3-chlorobenzamideAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A suspension of 8-chloro-1H-benzo[d][1,3]oxazine-2,4-dione (4.00 g, 20.3 mmol) and 3-bromo-2-methylaniline (5.65 g, 30.4 mmol) in xylene (20 mL) was heated at reflux for 2.5 h. The cooled mixture formed a yellow precipitate. The mixture was diluted with hexanes, and the precipitate was collected by filtration, washed with hexanes and dried to give 2-amino-N-(3-bromo-2-methylphenyl)-3-chlorobenzamide as a yellow solid (6.28 g, 91% yield). Mass spectrum m/z 339, 341 (M+H)+. 1H NMR (400 MHz, chloroform-d) δ 7.68 (d, J=8.1 Hz, 1H), 7.61 (br. s., 1H), 7.52-7.43 (m, 3H), 7.15 (t, J=8.0 Hz, 1H), 6.70 (t, J=7.8 Hz, 1H), 6.12 (br. s., 2H), 2.44 (s, 3H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 h
  3. customThe cooled mixture formed a yellow precipitate
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with hexanes
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a2331745b56c4071b9f61e1b7ef3b30d
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334290B2

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