Triethylamine → 4-(1-Bromo-cyclohexanoyl)-amino-2,3-dichloro-phenol

HRID 582721Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 582721
[Br:1][C:2]1([C:8](Cl)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.N[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([Cl:19])[C:13]=1[Cl:20].C([N:23](CC)CC)C>O1CCCC1>[Br:1][C:2]1([C:8]([C:12]2[C:17]([NH2:23])=[CH:16][C:15]([OH:18])=[C:14]([Cl:19])[C:13]=2[Cl:20])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 98775294-Amino-2,3-dichlorophenolHCID 152548741-Bromocyclohexanecarbonyl chloride

Produkt 1

HCID 867542704-(1-Bromo-cyclohexanoyl)-amino-2,3-dichloro-phenolAusbeute 64,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

12.6 g (0.056 mol) of 1-bromo-cyclohexanecarboxylic acid chloride are added dropwise at 0° C. with stirring to a mixture of 10 g (0.056 mol) of 4-amino-2,3-dichlorophenol and 100 ml of tetrahydrofuran. After adding half (5 g) of the acid chloride, 7.7 ml (0.05 mol) of triethylamine are added dropwise at the same time. When the addition has ended, the reaction mixture is stirred for 24 hours at 20° C. and then poured into 300 ml of ice-water. The mixture is extracted twice using in each case 300 ml of dichloromethane, and the organic phase is dried over magnesium sulphate and evaporated by stripping off the solvent under reduced pressure. The residue which remains is recrystallized from toluene. In this manner. 11.9 g (58% of theory) of 4-(1-bromo-cyclohexanoyl)-amino-2,3-dichloro-phenol are obtained in the form of a solid substance of melting point 142° C.

Aufarbeitung

  1. additionare added dropwise at the same time
  2. additionWhen the addition
  3. extractionThe mixture is extracted twice
  4. dry with materialthe organic phase is dried over magnesium sulphate
  5. customevaporated
  6. customThe residue which remains is recrystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-57ffef8609494f65947386a56af30e3f
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05925674

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