Methyl phenothiazin-2-yl ether → Di-p-toluoyltartaric acid

HRID 2291883

Reaktionsgleichung

Reaktionsgleichung von HRID 2291883
COC1C=CC2SC3C(=CC=CC=3)NC=2C=1.O.[C:18]1([CH3:45])[CH:23]=[CH:22][C:21]([C:24]([C@@:26]([C:42]([OH:44])=[O:43])([OH:41])[C@@:27]([C:32]([C:34]2[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=2)=[O:33])([OH:31])[C:28]([OH:30])=[O:29])=[O:25])=[CH:20][CH:19]=1>C(O)C>[C:18]1([CH3:45])[CH:23]=[CH:22][C:21]([C:24]([C:26]([C:42]([OH:44])=[O:43])([OH:41])[C:27]([C:32]([C:34]2[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][CH:39]=2)=[O:33])([OH:31])[C:28]([OH:30])=[O:29])=[O:25])=[CH:20][CH:19]=1

Komponenten

4

Edukt 2

HCID 74490Methyl phenothiazin-2-yl etherHCID 69630779(-)-di(p-toluoyl)-L-tartaric acid monohydrate

Produkt 1

HCID 12049127Di-p-toluoyltartaric acidAusbeute 134,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

(±)-10-(3 Dimethy]amino-2-methylpropyl)-2-methoxyphenothiazine (16.5 g; 0.05 mole), (-)-di(p-toluoyl)-L-tartaric acid monohydrate (10.15 g; 0.025 mole) and ethanol (75 cc) are introduced into a 250-cc three-necked round-bottomed flask equipped with a mechanical stirrer, a condenser and a nitrogen inlet. The stirred mixture is heated to 60° C. until a homogeneous solution is obtained. The mixture is cooled to 50° C. and crystallization is then seeded by adding a few crystals of the neutral salt of (-)-di(p-toluoyl)tartaric acid and the dextrorotatory base. While stirring is maintained, the mixture is kept for 1 hour at 50° C., cooled to 20° C. in the course of 2 hours, and maintained at 20° C. for 1 hour. The crystals obtained are separated by filtration, washed with ethanol (2×30 cc) and then dried. The neutral salt (12.99 g) of (-)-di(p-toluoyl)tartaric acid and dextrorotatory 10-(3-dimethylamino-2-methylpropyl) -2-methoxyphenothiazine is thereby obtained.

Aufarbeitung

  1. customequipped with a mechanical stirrer, a condenser and a nitrogen inlet
  2. customis obtained
  3. temperatureThe mixture is cooled to 50° C.
  4. customcrystallization
  5. additionby adding a few crystals of the neutral salt of (-)-di(p-toluoyl)tartaric acid
  6. temperatureis maintained
  7. temperaturecooled to 20° C. in the course of 2 hours
  8. temperaturemaintained at 20° C. for 1 hour
  9. customThe crystals obtained
  10. customare separated by filtration
  11. washwashed with ethanol (2×30 cc)
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-63c8329539be4d6c91c0ebc0460b13c8
Quelldatensatz
uspto-grants-1989_01
Patentnummer
US04798895

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