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

HRID 2067177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2067177
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>CN1C(=O)CCC1.CCOC(C)=O>[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 3

HCID 76688CyclohexanemethylamineHCID 81531DiisopropylethylamineHCID 2731322-Chloro-6-methoxybenzothiazole

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
107.5 °C

Versuchsvorschrift

To a 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 diluted with EtOAc (250 mL) and washed with saturated NaHCO3 (2×60 mL), water (3×60 mL), saturated NaCl (60 mL), dried with sodium sulfate, filtered and concentrated in vacuo to give N-(cyclohexylmethyl)-6-methoxybenzo[d]thiazol-2-amine as a solid (1.18 grams). ES/MS m/z 277.1 (MH+).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f16efb7fbb7f4ff1bec3623a736d8a5b
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293769B2

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