2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 178456711, Verbindung

HRID 979315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 979315
[OH:1][C:2]1[CH:15]=[C:14]2[C:5]([NH:6][C:7]3[C:12]([S:13]2(=[O:17])=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]=12.ClC1C(=O)[C:25](C#N)=[C:26]([C:31]#[N:32])C(=O)C=1Cl.C(N)CC>C1COCC1>[CH2:31]([NH:32][C:15]1[C:2](=[O:1])[C:3]2[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=2[C:5]2[C:14]=1[S:13](=[O:17])(=[O:16])[C:12]1[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[N:6]=2)[CH2:26][CH3:25]

Komponenten

5

Edukt 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 7852PropylamineHCID 137124805-Hydroxy-12H-benzo[a]phenothiazine-7,7-dioxide

Produkt 1

HCID 178456711HCID 178456711, VerbindungAusbeute 62,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 5-hydroxy-12H-benzo[a]phenothiazine-7,7-dioxide (594 mg) in THF (10 ml) was added 2,3-dichloro 5,6-dicyano-1,4-benzoquinone (1.021 gram). The mixture was stirred at room temperature for 2 minutes, then there was added n-propyl amine (0.2 ml). The stirring was continued for 0.5 hour, then the mixture was evaporated to dryness. To the residue was added 50 ml dichloromethane and the mixture was stirred for 15 minutes and filtered. The filtrate was evaporated to dryness and the residue crystallized from a mixture of toluene and hexane to afford the title compound (442 mg) as a red-brown crystalline solid, m.p. 149°-151° C. (dec.).

Aufarbeitung

  1. waitThe stirring was continued for 0.5 hour
  2. customthe mixture was evaporated to dryness
  3. additionTo the residue was added 50 ml dichloromethane
  4. stirringthe mixture was stirred for 15 minutes
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue crystallized from a mixture of toluene and hexane

Quellen und Nachweise

ORD-Eintrag
ord-4c457c88b89346088d00c22d419648ef
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04667032

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