Hydrochloric Acid → Naphtho(1,2-d)thiazol-2-amine, 4,5-dihydro-N-(2-(4-morpholinyl)ethyl)-, dihydrochloride

HRID 1768550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1768550
[C:1]([NH:9][C:10]([NH:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[S:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[ClH:23].Br[CH:25]1[CH2:34]CC2C(=CC=CC=2)[C:26]1=O>C(O)C>[ClH:23].[ClH:23].[O:18]1[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][NH:12][C:10]2[S:11][C:26]3[CH2:25][CH2:34][C:7]4[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:1]=3[N:9]=2)[CH2:16][CH2:17]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1011201(2H)-Naphthalenone, 2-bromo-3,4-dihydro-HCID 805795HCID 805795, Verbindung

Produkt 1

HCID 3088648Naphtho(1,2-d)thiazol-2-amine, 4,5-dihydro-N-(2-(4-morpholinyl)ethyl)-, dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

3.66 g of N-benzoyl-N'-(morpholinoethyl)thiourea are refluxed in 17.5 ml of a 2.5N solution of sodium hydroxide under a nitrogen atmosphere for 15 minutes. After cooling, concentrated hydrochloric acid is added until the pH is 7. A solution of 3 g of 2-bromo-1,2,3,4-tetrahydronaphthalen-1-one in 20 ml of ethanol is added and the mixture is refluxed for 1 hour. After evaporation of the solvent, the residue is neutralized by the addition of sodium bicarbonate and extraction is carried out twice with methylene chloride. The organic phase is dried over magnesium sulfate and chromatographed on a silica column by elution with a methylene chloride/methanol mixture (95/5 vol/vol).

Aufarbeitung

  1. temperatureAfter cooling
  2. temperaturethe mixture is refluxed for 1 hour
  3. customAfter evaporation of the solvent
  4. additionthe residue is neutralized by the addition of sodium bicarbonate and extraction
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. customchromatographed on a silica column by elution with a methylene chloride/methanol mixture (95/5 vol/vol)

Quellen und Nachweise

ORD-Eintrag
ord-5812f9c376c94ec0a75dceca315dfed9
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05378706

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