Hydroquinone → 3-(Benzothiazol-6-ylamino)-2-methyl-propionic Acid

HRID 2383904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2383904
[CH3:1][C:2](=[CH2:6])[C:3]([OH:5])=[O:4].C1(O)C=CC(O)=CC=1.[S:15]1[C:19]2[CH:20]=[C:21]([NH2:24])[CH:22]=[CH:23][C:18]=2[N:17]=[CH:16]1.CO>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[S:15]1[C:19]2[CH:20]=[C:21]([NH:24][CH2:6][CH:2]([CH3:1])[C:3]([OH:5])=[O:4])[CH:22]=[CH:23][C:18]=2[N:17]=[CH:16]1

Komponenten

7

Edukt 4

HCID 785HydroquinoneHCID 887MethanolHCID 4093Methacrylic AcidHCID 682886-Aminobenzothiazole

Produkt 1

HCID 687859923-(Benzothiazol-6-ylamino)-2-methyl-propionic AcidAusbeute 27,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-Methyl-acrylic acid (0.63 g, 0.00732 mol) and Benzene-1,4-diol (0.029 g, 0.000266 mol) were added to a stirred solution of Benzothiazol-6-ylamine (1 g, 0.00665 mol) in toluene (6 mL) under nitrogen atmosphere. The resulting reaction mass was heated at 70° C. for 72 hours and further at 100° C. for 48 hours. The reaction was monitored by TLC (5% methanol in chloroform). The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford the crude product. Purification by column chromatography on silica gel (0.75% methanol in chloroform) afforded 0.43 g of the product (26.87% yield).

Aufarbeitung

  1. customThe resulting reaction mass
  2. temperatureThe reaction mixture was cooled to room temperature
  3. custompartitioned between water and ethyl acetate
  4. washThe organic layer was washed with brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto afford the crude product
  8. customPurification by column chromatography on silica gel (0.75% methanol in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-b54d83c782fd4fb889acb1af7310bbcc
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263635B2

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