Water → 4-Phenoxy-1,3-benzothiazol-2-amine

HRID 1164518Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1164518
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([NH2:17])=[S:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrBr.O.[OH-].[Na+]>C(Cl)(Cl)Cl>[NH2:17][C:15]1[S:16][C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:9]=2[N:14]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24408BromineHCID 1479735(2-Phenoxyphenyl)thiourea

Produkt 1

HCID 130970824-Phenoxy-1,3-benzothiazol-2-amineAusbeute 48,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a mixture of 1-(2-phenoxyphenyl)thiourea (53.4 g) in chloroform (100 ml) was added dropwise a solution of bromine (35.0 g) in chloroform (50 ml) with stirring under ice-cooling during 40 minutes. After refluxing for 1 hour and 40 minutes, the mixture was cooled to ambient temperature. To the resultant mixture was added water and then the mixture was alkalified with 5% sodium hydroxide aqueous solution. The chloroform layer was washed with water, dried over magnesium sulfate, concentrated under reduced pressure to give crystals, which were recrystallized twice from isopropyl alcohol to give 2-amino-4-phenoxybenzothiazole (25.8 g).

Aufarbeitung

  1. temperaturecooling during 40 minutes
  2. temperatureAfter refluxing for 1 hour and 40 minutes
  3. washThe chloroform layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give crystals, which
  7. customwere recrystallized twice from isopropyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-b4ee5edafba64c9b8e0194127683e6d7
Quelldatensatz
uspto-grants-1983_01
Patentnummer
US04370340

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