3,5-Dimethylaniline → 2-[(5,7-Dimethylbenzothiazol-2-ylimino)methylene]propanedinitrile

HRID 2412342

Reaktionsgleichung

Reaktionsgleichung von HRID 2412342
CC1C=C(C=C(C)C=1)N.[S-]C#N.[NH4+].[CH3:14][C:15]1[CH:16]=[C:17]([NH:22][C:23]([NH2:25])=[S:24])[CH:18]=[C:19]([CH3:21])[CH:20]=1.BrBr.[NH2:28][C:29]1[S:30][C:31]2[C:37]([CH3:38])=[CH:36][C:35]([CH3:39])=[CH:34][C:32]=2[N:33]=1.[Na].C(O[CH:44]=[C:45]([C:48]#[N:49])[C:46]#[N:47])C>C(O)C.C(Cl)(Cl)Cl>[NH2:25][C:23]1[S:24][C:18]2[C:19]([CH3:21])=[CH:20][C:15]([CH3:14])=[CH:16][C:17]=2[N:22]=1.[CH3:39][C:35]1[CH:36]=[C:37]([CH3:38])[C:31]2[S:30][C:29]([N:28]=[C:44]=[C:45]([C:48]#[N:49])[C:46]#[N:47])=[N:33][C:32]=2[CH:34]=1

Komponenten

11

Edukt 7

HCID 79493,5-DimethylanilineHCID 15666Ammonium thiocyanateHCID 24408BromineHCID 671522-(Ethoxymethylene)propanedinitrileHCID 736215(3,5-Dimethylphenyl)thioureaHCID 20498965,7-Dimethyl-1,3-benzothiazol-2-amineHCID 5360545Sodium

Produkt 2

HCID 20498965,7-Dimethyl-1,3-benzothiazol-2-amineHCID 204330602-[(5,7-Dimethylbenzothiazol-2-ylimino)methylene]propanedinitrileAusbeute 72,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

2-Amino-5,7-dimethylbenzothiazole was prepared by treatment of 3,5-dimethylaniline with ammonium thiocyanate and conversion of the resulting N-(3,5-dimethylphenyl)thiourea with bromine and chloroform (Barnikow and Bodeker Ber. 100(5), 1394), m.p. 142°-144°. 2-Amino-5,7-dimethylbenzothiazole, 6.16 g. (34.5 millimoles) was added to a solution of a pea-sized piece of sodium in 40 ml. of anhydrous ethanol. Ethoxymethylenemalononitrile, 4.22 g. (34.5 millimoles), was added to the solution and the mixture was heated at reflux for about 2 hrs. The precipitated solid was collected by filtration, washed with ethanol, and dried in vacuo at 100°, yielding 6.93 g. (72.7%) of the desired product which was a yellow solid, m.p. 239°-241°. A small portion was recrystallized from 95% ethanol and submitted for analysis, m.p. 241°-243°.

Aufarbeitung

  1. addition(34.5 millimoles), was added to the solution
  2. temperaturethe mixture was heated
  3. temperatureat reflux for about 2 hrs
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with ethanol
  6. customdried in vacuo at 100°
  7. customyielding 6.93 g
  8. customA small portion was recrystallized from 95% ethanol

Quellen und Nachweise

ORD-Eintrag
ord-af1fd4ce1aa147b7be794f955a196df1
Quelldatensatz
uspto-grants-1985_01
Patentnummer
US04491587

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