Carbon Disulfide → Metiamide

HRID 372269Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 372269
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].[CH:12]1([N:18]=[C:19]=NC2CCCCC2)CCCCC1.C(=S)=[S:28]>N1C=CC=CC=1>[CH3:12][NH:18][C:19]([NH:11][CH2:10][CH2:9][S:8][CH2:7][C:3]1[N:4]=[CH:5][NH:6][C:2]=1[CH3:1])=[S:28]

Komponenten

5

Edukt 3

HCID 6348Carbon DisulfideHCID 10868DicyclohexylcarbodiimideHCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazole

Produkt 1

HCID 1548992Metiamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel2×

Versuchsvorschrift

A solution of 2-((5-methyl-4-imidazolyl)methylthio)ethylamine (3.42 g 0.02 mol) in dry pyridine (15 ml) was slowly added under dry nitrogen to a stirred solution of N,N'-dicyclohexylcarbodiimide (4.12 g 0.02 mol) and carbon disulphide (20 ml) in dry pyridine (10 ml) at -10°. The mixture was stirred for 4 hours at -10° and 18 hours at room temperature and was filtered. The filtrate was evaporated to dryness and the residue was dissolved in warm acetonitrile and the solution was cooled, filtered and the filtrate was evaporated to dryness. The residue was boiled for five minutes with an excess of aqueous methylamine. The solid which crystallised on cooling was recrystallised from water to give N-methyl-N'-[2-(5-methyl-4-imidazolylmethylthio)ethyl]thiourea.

Aufarbeitung

  1. filtrationwas filtered
  2. customThe filtrate was evaporated to dryness
  3. dissolutionthe residue was dissolved in warm acetonitrile
  4. temperaturethe solution was cooled
  5. filtrationfiltered
  6. customthe filtrate was evaporated to dryness
  7. waitThe residue was boiled for five minutes
  8. customThe solid which crystallised
  9. temperatureon cooling
  10. customwas recrystallised from water

Quellen und Nachweise

ORD-Eintrag
ord-d1717f6fb9614bc78686e243b654e867
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04090026

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