Dimethylamine → 3-(5,5-Dimethyl-7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-1,1-dimethyl-urea

HRID 595080

Reaktionsgleichung

Reaktionsgleichung von HRID 595080
[NH2:1][C:2]1[S:3][C:4]2[C:10](=[O:11])[CH2:9][C:8]([CH3:13])([CH3:12])[CH2:7][C:5]=2[N:6]=1.C1N=[CH:17][N:16]([C:19](N2C=NC=C2)=[O:20])[CH:15]=1.C1CCN2C(=NCCC2)CC1.CNC>C(#N)C>[CH3:12][C:8]1([CH3:13])[CH2:7][C:5]2[N:6]=[C:2]([NH:1][C:19](=[O:20])[N:16]([CH3:17])[CH3:15])[S:3][C:4]=2[C:10](=[O:11])[CH2:9]1

Komponenten

6

Edukt 4

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5878742-Amino-5,5-dimethyl-5,6-dihydro-4H-benzothiazol-7-one

Produkt 1

HCID 205043303-(5,5-Dimethyl-7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-1,1-dimethyl-ureaAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 2-amino-5,5-dimethyl-5,6-dihydro-4H-benzothiazol-7-one (151 g, 0.768 mol) in acetonitrile (5 L) are added CDI (249 g, 1.53 mol) and DBU (233 g, 1.53 mol). The reaction mixture is stirred overnight at 100° C. Dimethylamine (310 g, 3.83 mol) is added at RT and the stirring is continued overnight at 100° C. After cooling to RT, the reaction mixture is concentrated in vacuo and the residue is poured into ice water. The pH of the mixture is adjusted to pH 5 with HCl (6 M). The aqueous mixture is extracted with ethyl acetate (4×500 mL). The combined organic layers are washed with brine (500 mL) and dried over anhydrous Na2SO4. The solvent is evaporated in vacuo to give crude product. The crude product is washed with water to give 3-(5,5-dimethyl-7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-1,1-dimethyl-urea (169 g, 82% yield).

Aufarbeitung

  1. waitthe stirring is continued overnight at 100° C
  2. temperatureAfter cooling to RT
  3. concentrationthe reaction mixture is concentrated in vacuo
  4. additionthe residue is poured into ice water
  5. extractionThe aqueous mixture is extracted with ethyl acetate (4×500 mL)
  6. washThe combined organic layers are washed with brine (500 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe solvent is evaporated in vacuo
  9. customto give crude product
  10. washThe crude product is washed with water

Quellen und Nachweise

ORD-Eintrag
ord-6999cae8d4f342d0ae16606ad2a34978
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09243000B2

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