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Benzo(d)thiazol-2-amine → 1-(1,3-Benzothiazol-2-yl)propan-2-one

HRID 4702
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 4702
N[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[OH-:11].[Na+].[Na].[K].S[C:16]1[CH:21]=CC=C[C:17]=1NC(N)=O>C(O)(=O)C.C=C1OC(=O)C1.O>[CH2:17]([C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1)[C:16]([CH3:21])=[O:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 8706Benzo(d)thiazol-2-amineHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 5462222PotassiumHCID 23358470N-(2-Sulfanylphenyl)urea

Produkt 1

HCID 3202941-(1,3-Benzothiazol-2-yl)propan-2-oneAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel2×HCID 12661DiketeneLösungsmittel

Versuchsvorschrift

The water-moist 2-mercaptophenylurea obtained according to European Pat. No. 0,039,483, Example 1, paragraph 1, by reacting 150 parts of 2-aminobenzothiazole with 150 parts of sodium hydroxide and working up the mixture with water, or an appropriate amount of the sodium or potassium salt of the said 2-mercaptophenylurea, is dissolved in 500 parts of 50% strength acetic acid, and 118 parts of diketene are then added dropwise in the course of 2 hours at 45° to 50° C. Stirring is continued for 1 hour, after which the mixture is heated to the reflux temperature and kept at a temperature of 95° C.-100° C. for 2 hours. It is then cooled to room temperature, and the precipitated 2-acetonylbenzothiazole of the formula ##STR13## is isolated by filtration and dried in vacuo at 60° C.-80° C. 151.7 parts of a product of melting point 118° C.-119° C. are obtained; this corresponds to a yield of 79.4%, based on 2-aminobenzothiazole employed.

Aufarbeitung

  1. additionare then added dropwise in the course of 2 hours at 45° to 50° C
  2. temperatureafter which the mixture is heated to the reflux temperature
  3. waitkept at a temperature of 95° C.-100° C. for 2 hours

Quellen und Nachweise

ORD-Eintrag
ord-3f4e5fd49dba41ce9980468ba16d9ddd
Quelldatensatz
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04727154

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