p-Toluenesulfonic acid → HCID 19360973, Verbindung

HRID 376229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 376229
[C:1]([C:5]1[C:6]([SH:16])=[C:7]([CH:9]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=1)[NH2:8])([CH3:4])([CH3:3])[CH3:2].C(C1C=[C:23]([CH:27]=C(C(C)(C)C)C=1)[C:24]([OH:26])=[O:25])(C)(C)C.[C:34]1(C)C=CC(S(O)(=O)=O)=C[CH:35]=1>CO>[C:12]([C:10]1[CH:11]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]2[S:16][C:27]([CH2:23][C:24]([O:26][CH2:34][CH3:35])=[O:25])=[N:8][C:7]=2[CH:9]=1)([CH3:15])([CH3:14])[CH3:13]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 853393,5-Bis(tert-butyl)benzoic acidHCID 12087014HCID 12087014, Verbindung

Produkt 1

HCID 19360973HCID 19360973, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 40 g of 3,5-di(t-butyl)-2-mercaptoaniline [prepared according to a literature procedure from 3,5-di(t-butyl)benzoic acid] and 75 mL of ethyl 3-(trimethoxy)propionate in 1.2 L of methanol containing 1.5 g of p-toluenesulfonic acid was stirred at r.t. for 18 h. Excess methanol was removed by rotary evaporation. The precipitated the solid was filtered and washed with cold methanol. The crude product was purified by flash chromatography on silica gel and eluted with heptane to give 20 g of ethyl 2-[5,7-di(t-butyl)benzothiazolyl]acetate. The latter was refluxed with 16 g of 1,1,7,7-tetramethyl-8-hydroxy-9-formyljulolidine in 200 mL of acetonitrile containing 4 mL of piperidine for 18 h. The reaction mixture was cooled and the precipitated bright orange solid was filtered to give 13 g of the desired dye C-545TB: m.p. 275-276° C.; Tg=140° C.

Aufarbeitung

  1. customprepared
  2. customExcess methanol was removed by rotary evaporation
  3. customThe precipitated the solid
  4. filtrationwas filtered
  5. washwashed with cold methanol
  6. customThe crude product was purified by flash chromatography on silica gel
  7. washeluted with heptane

Quellen und Nachweise

ORD-Eintrag
ord-7b439c4485154a7787245cc35d75960c
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06020078

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