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Hydrochloric Acid → Benzenamine, 3-(2,3,5,6-tetrahydroimidazo(2,1-b)thiazol-6-yl)-, dihydrochloride, (+-)-

HRID 597574
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 597574
[S:1]1[CH2:5][CH2:4][N:3]2[CH2:6][CH:7]([C:9]3[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=3)[NH:12]C(=O)C)[N:8]=[C:2]12.[ClH:19]>CO.CC(O)C>[ClH:19].[ClH:19].[NH2:12][C:11]1[CH:10]=[C:9]([CH:7]2[CH2:6][N:3]3[C:2]([S:1][CH2:5][CH2:4]3)=[N:8]2)[CH:18]=[CH:17][CH:16]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 313Hydrochloric Acid2×HCID 128505123'-(2,3,5,6-Tetrahydroimidazo[2,1-b]thiazol-6-yl)acetanilide

Produkt 1

HCID 3038668Benzenamine, 3-(2,3,5,6-tetrahydroimidazo(2,1-b)thiazol-6-yl)-, dihydrochloride, (+-)-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of 1.00 g. (0.0038 mole) of 3'-(2,3,5,6-tetrahydroimidazo[2,1-b]thiazol-6-yl)acetanilide (Example 8) in 17 ml. of 6N hydrochloric acid is heated at reflux for 2.5 hours and then allowed to stand overnight at room temperature. The solution is concentrated at reduced pressure, made basic with concentrated aqueous sodium hydroxide while cooling and then extracted with 3 portions of chloroform. The combined organic layers are washed with brine, dried (sodium sulfate) and evaporated to give 0.84 g. of an oil, i.e., m-aminotetramisole free base. The oil is dissolved in hot methanol and strongly acidified with hydrogen chloride in 2-propanol. Evaporation of the solution and crystallization of the residue from 2-propanol gives 0.91 g. (81%) of cream colored solid, melting point 198°-201° C., dec.

Aufarbeitung

  1. temperatureat reflux for 2.5 hours
  2. concentrationThe solution is concentrated at reduced pressure
  3. temperaturewhile cooling
  4. extractionextracted with 3 portions of chloroform
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried (sodium sulfate)
  7. customevaporated
  8. customto give 0.84 g
  9. customEvaporation of the solution and crystallization of the residue from 2-propanol
  10. customgives 0.91 g

Quellen und Nachweise

ORD-Eintrag
ord-a94c9eae0dbe45aaab3357ae7188520f
Quelldatensatz
uspto-grants-1977_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04014892

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