Toluene → S-(1-Phenyl-5-tetrazolyl) chlorothioformate

HRID 1085051

Reaktionsgleichung

Reaktionsgleichung von HRID 1085051
[C:1]([Cl:4])(Cl)=[O:2].C1(C)C=CC=CC=1.C(N(CC)CC)C.[C:19]1([N:25]2[C:29]([SH:30])=[N:28][N:27]=[N:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[Cl:4][C:1]([S:30][C:29]1[N:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:26]=[N:27][N:28]=1)=[O:2]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 6371PhosgeneHCID 8471TriethylamineHCID 1785279861-phenyltetrazole-5-thiol

Produkt 1

HCID 86028543S-(1-Phenyl-5-tetrazolyl) chlorothioformateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

A 20% phosgene solution in toluene (14.4 ml, 25.2 mmole) was added to a mixture of triethylamine (2.58 ml, 18.5 mmol) and 1-phenyl-1H-tetrazol-5-thiol (3.00 g, 16.8 mmole) in THF (15 ml) at 5° C. over 10 min. The reaction mixture was stirred for an hour at 5° C. and filtered. The filtrate obtained was evaporated and the residue washed thoroughly with ethyl ether. It was then recrystallized by dissolving in THF and precipitating with ethyl ether to give white crystal (2.92 g, 72%) m.p. 112°-114° C. IR (Film) 1718, 1645, 1590, 1490 and 1395 cm-1. 1H-NMR (CDCl3) δ7.52 (s, aromatic H).

Aufarbeitung

  1. filtrationfiltered
  2. customThe filtrate obtained
  3. customwas evaporated
  4. washthe residue washed thoroughly with ethyl ether
  5. customIt was then recrystallized
  6. dissolutionby dissolving in THF
  7. customprecipitating with ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-1303abd955924b758a34f64d6d910e9e
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05008245

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