2,5-Dibromoterephthalic acid → 2,5-Dibromo-4-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-carbonyl)-benzoic acid

HRID 1943661

Reaktionsgleichung

Reaktionsgleichung von HRID 1943661
[Br:1][C:2]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[C:8]([Br:14])=[CH:7][C:3]=1[C:4]([OH:6])=O.BrC1C=C(C(Cl)=O)C(Br)=CC=1C(Cl)=O.[O:29]1[CH2:34][CH2:33][NH:32][C:31]2[CH:35]=[N:36][CH:37]=[CH:38][C:30]1=2>CN(C)C=O.S(Cl)(Cl)=O.ClCCl.C(N(CC)CC)C>[Br:14][C:8]1[CH:7]=[C:3]([C:4]([N:32]2[CH2:33][CH2:34][O:29][C:30]3[CH:38]=[CH:37][N:36]=[CH:35][C:31]2=3)=[O:6])[C:2]([Br:1])=[CH:10][C:9]=1[C:11]([OH:13])=[O:12]

Komponenten

8

Edukt 3

HCID 836902,5-Dibromoterephthalic acidHCID 218859502H,3H,4H-pyrido[4,3-b][1,4]oxazineHCID 229969282,5-Dibromobenzene-1,4-dicarbonyl dichloride

Produkt 1

HCID 446088742,5-Dibromo-4-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-carbonyl)-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6228DimethylformamideKatalysatorHCID 8471TriethylamineKatalysatorHCID 6344DichloromethaneLösungsmittel2×HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

In a 20 ml flask, 2,5-dibromo-terephthalic acid (100 mg, 0.31 mmol) and N,N-dimethyl formamide (3 drops) were dissolved in thionyl chloride (2 ml). After stirring for 2 hours at 800, the reaction mixture was cooled to room temperature and concentrated. Crude 2,5-dibromo-terephthaloic dichloride (112 mg, 0.31 mmol) was dissolved in dichloromethane (6 ml) and was added to 3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (20.9 mg, 0.15 mmol) dissolved in dichloromethane (1 ml). Triethylamine (3 drops) were slowly added thereto and stirred at room temperature for 16 hours. After completion of the reaction, the residue was purified by preparative LC/Mass to obtain the target compound 23, i.e., 2,5-dibromo-4-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-carbonyl)-benzoic acid, as white solid (23 mg, 5%).

Aufarbeitung

  1. concentrationconcentrated
  2. stirringstirred at room temperature for 16 hours
  3. customAfter completion of the reaction
  4. customthe residue was purified by preparative LC/Mass

Quellen und Nachweise

ORD-Eintrag
ord-1c2ed47af75544758399639936b77033
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394792B2

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