Sodium Hydroxide → 3-(2-Thiazolyl)propylguanidine hemisulphate

HRID 372015

Reaktionsgleichung

Reaktionsgleichung von HRID 372015
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][CH2:7][CH2:8][NH2:9].[OH-].[Na+].[S:12]([O-:16])([O-:15])(=[O:14])=[O:13].CS[C:19]([NH2:21])=[NH2+:20].CS[C:24]([NH2:26])=[NH2+:25]>C(OCC)(=O)C>[S:12]([OH:16])([OH:15])(=[O:14])=[O:13].[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][CH2:7][CH2:8][NH:9][C:19]([NH2:21])=[NH:20].[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][CH2:7][CH2:8][NH:9][C:24]([NH2:26])=[NH:25]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 6604939S-methyl isothiourea hemisulfateHCID 116869213-(1,3-Thiazol-2-yl)propan-1-amine

Produkt 1

HCID 1785127923-(2-Thiazolyl)propylguanidine hemisulphate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3-phthalimidothiobutyramide (15.0 g) and bromoacetaldehyde diethyl acetal (19.7 g) is heated at 100° C with frequent agitation for two hours. The solid mass is extracted with hot ethanol, and the extracts are treated with charcoal and filtered. On cooling, crystals are deposited. These are dissolved in water (50 ml) and the solution washed with ether (25 ml) and diluted with aqueous sodium acetate to pH 6. A yellowish-brown solid crystallizes out which is collected and washed with water yielding 3-(2-thiazolyl)propylphthalimide hydrobromide, m.p. 67°-70° C. The phthalimido derivative (5.0 g) is dissolved in ethanol (50 ml), hydrazine hydrate (2 ml) is added and the solution heated under reflux for two hours. The solvent is removed under reduced pressure and the residue is dissolved in concentrated hydrochloric acid (30 ml) and heated under reflux for one hour. After cooling, phthalhydrazide is removed by filtration and the filtrate evaporated to dryness. The residue is recrystallized from methanol-ether yielding 3-(2-thiazolyl) propylamine dihydrochloride, m.p. 160°-165° C. 3-(2-Thiazolyl)propylamine (2.7 g) (prepared from the amine dihydrochloride by reaction with aqueous sodium hydroxide and extraction with ethyl acetate) is mixed intimately with finely powdered S-methyl-thiouronium sulphate (5.3 g) and the mixture is heated at 140°-150° C for one hour. After cooling, the mass is extracted with hot ethanol several times, and the combined extracts are diluted with ether which causes the precipitation of a white solid. Recrystallization from aqueous ethanol yields 3-(2-thiazolyl)propylguanidine hemisulphate, m.p. 160°-163° C.

Aufarbeitung

  1. temperaturethe mixture is heated at 140°-150° C for one hour
  2. temperatureAfter cooling
  3. extractionthe mass is extracted with hot ethanol several times
  4. additionthe combined extracts are diluted with ether which
  5. customthe precipitation of a white solid
  6. customRecrystallization from aqueous ethanol

Quellen und Nachweise

ORD-Eintrag
ord-c8dac9d18431449eb9c6bceb3e8a6157
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04088769

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