Ethyl Acetate → N-(cyclohexylmethyl)-6-methoxy-1,3-benzothiazol-2-amine

HRID 1922254Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922254
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:13]1([CH2:19][NH2:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.CCN(C(C)C)C(C)C.C(OCC)(=O)C>CN1C(=O)CCC1>[CH:13]1([CH2:19][NH:20][C:2]2[S:3][C:4]3[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=3[N:6]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 76688CyclohexanemethylamineHCID 81531DiisopropylethylamineHCID 2731322-Chloro-6-methoxybenzothiazole

Produkt 1

HCID 57725688N-(cyclohexylmethyl)-6-methoxy-1,3-benzothiazol-2-amineAusbeute 94,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
107.5 °C

Versuchsvorschrift

To the solution of 2-chloro-6-methoxybenzo[d]thiazole (900 mg, 4.5 mmol) in 4.5 ml of NMP was added cyclohexylmethanamine (865 mg, 7.65 mmol) and DIPEA (1.57 ml, 9.0 mmol). The reaction solution was stirred at 105-110° C. for 66 hours. The reaction was worked up by adding 250 ml ethyl acetate and washed with 2×60 ml of saturated NaHCO3, 3×60 ml water, 1×60 ml saturated NaCl, dried with sodium sulfate, filtered and concentrated in vacuo to give N-(cyclohexylmethyl)-6-methoxybenzo[d]thiazol-2-amine as solid (1.18 grams). ES/MS m/z 277.1 (MH+).

Aufarbeitung

  1. washwashed with 2×60 ml of saturated NaHCO3, 3×60 ml water, 1×60 ml saturated NaCl
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-06fda797a4b5466aa24b98ad7496fca5
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173689B2

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