Hydrochloric Acid → 2-Chloro-6-ethoxybenzo[d]thiazole

HRID 581050

Reaktionsgleichung

Reaktionsgleichung von HRID 581050
N[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH2:12][CH3:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.N([O-])=O.[Na+].[ClH:18]>C(O)(=O)C.O>[Cl:18][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH2:12][CH3:13])[CH:8]=[CH:7][C:5]=2[N:6]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric Acid2×HCID 7192Amino-6-ethoxybenzothiazole, 2-HCID 23668193Sodium Nitrite

Produkt 1

HCID 3500152-Chloro-6-ethoxybenzo[d]thiazoleAusbeute 61,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

20 g (0.103 mol) of 2-amino-6-ethoxy-benzothiazole are dissolved in 100 ml of glacial acetic acid and 52 ml of concentrated hydrochloric acid and whilst cooling with ice the mixture is diazotised with 7.4 g (0.108 mol) of sodium nitrite in 15 ml of water. Then the solution of the diazonium salt is added batchwise to a suspension of 13.6 g (0.137 mol) of copper-I-chloride in 65 ml of concentrated hydrochloric acid and stirred for 20 minutes at 30° C. Then the mixture is diluted with 800 ml of ice water and the crystals formed are suction filtered. To purify them they are chromatographed on silica gel (eluant: petroleum ether/ethyl acetate=6:1). Yield: 61.7% of theory, Melting point: 60-61° C.

Aufarbeitung

  1. customthe crystals formed
  2. customTo purify them they
  3. customare chromatographed on silica gel (eluant: petroleum ether/ethyl acetate=6:1)

Quellen und Nachweise

ORD-Eintrag
ord-90a8b040555d4ef5920bef665edef3e6
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05919807

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