Hydrochloric Acid → 2,5-Dimethoxyphenyl isothiocyanate

HRID 231029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 231029
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1[NH2:5].C(N(CC)CC)C.[C:19](=S)=[S:20].C1(N=C=NC2CCCCC2)CCCCC1.Cl>O1CCCC1.CCCCCC>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1[N:5]=[C:19]=[S:20]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 76132,5-DimethoxyanilineHCID 8471TriethylamineHCID 10868Dicyclohexylcarbodiimide

Produkt 1

HCID 1424662,5-Dimethoxyphenyl isothiocyanateAusbeute 57,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of 2,5-dimethoxyaniline (61.2 g, 0.4 mol) and triethylamine (75 ml, 0.48 mol) in 300 ml of tetrahydrofuran was added carbon disulfide (91.2 g, 0.48 mol) at 5° C. and stirring was continued for 3 hours. To the reaction mixture kept at 5° C. was added N,N'-dicyclohexylcarbodiimide (99 g, 0.48 mol) and stirring was continued for another 3 hours. To the reaction mixture were added 2N HCl solution (100 ml) and hexane (100 ml) and an aqueous layer was separated. n-Hexane (100 ml) was further added to an organic layer and precipitates were filtered off. The solvents were distilled off under reduced pressure and a crude oily product was obtained. Separation and purification by chromatography using a silica gel column gave oily 2,5-dimethoxyphenylisothiocyanate (45 g, yield 57%).

Aufarbeitung

  1. customkept at 5° C.
  2. stirringstirring
  3. waitwas continued for another 3 hours
  4. customan aqueous layer was separated
  5. additionn-Hexane (100 ml) was further added to an organic layer
  6. customprecipitates
  7. filtrationwere filtered off
  8. distillationThe solvents were distilled off under reduced pressure
  9. customa crude oily product was obtained
  10. customSeparation and purification by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-39634db7d4e0494d8363146a9ccc688e
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04845020

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