Riluzole → 2(3H)-Benzothiazolimine, 3-(cyclopropylmethyl)-6-(trifluoromethoxy)-, monohydrobromide

HRID 1111368

Reaktionsgleichung

Reaktionsgleichung von HRID 1111368
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.[Br:16][CH2:17][CH:18]1[CH2:20][CH2:19]1>CC(O)C>[BrH:16].[CH:18]1([CH2:17][N:6]2[C:5]3[CH:7]=[CH:8][C:9]([O:11][C:12]([F:15])([F:13])[F:14])=[CH:10][C:4]=3[S:3][C:2]2=[NH:1])[CH2:20][CH2:19]1

Komponenten

4

Edukt 2

HCID 5070RiluzoleHCID 81503Bromomethylcyclopropane

Produkt 1

HCID 30764082(3H)-Benzothiazolimine, 3-(cyclopropylmethyl)-6-(trifluoromethoxy)-, monohydrobromideAusbeute 8,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

The procedure is as in Example 15, starting with 2-amino-6-trifluoromethoxybenzothiazole (9.4 g) and bromomethylcyclopropane (12.7 g) in 2-propanol (30 cc). The mixture is heated for 42 hours to boiling. After cooling of the reaction medium to a temperature in the region of 20° C., the precipitate is filtered off and recrystallized in a boiling mixture (30 cc) of ethyl acetate and methanol (80:20 by volume). 3-Cyclopropylmethyl-2-imino-6-trifluoromethoxybenzothiazoline hydrobromide (1.2 g), m.p. 220° C., is obtained.

Aufarbeitung

  1. temperatureThe mixture is heated for 42 hours
  2. filtrationthe precipitate is filtered off
  3. customrecrystallized in a boiling mixture (30 cc) of ethyl acetate and methanol (80:20 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-e0b04e852d8c41e7a4cdf372b76997f7
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04980356

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