2-Amino-4-methylbenzothiazole → N1-(4-methyl-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxy phenyl)-1-propenyl]phenoxy}acetamide

HRID 512566

Reaktionsgleichung

Reaktionsgleichung von HRID 512566
[CH3:1][C:2]1[C:7]2[N:8]=[C:9]([NH2:11])[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH3:33][O:34][C:35]1[CH:45]=[CH:44][C:43](/[CH:46]=[CH:47]/[C:48](=[O:61])[C:49]2[CH:54]=[C:53]([O:55][CH3:56])[C:52]([O:57][CH3:58])=[C:51]([O:59][CH3:60])[CH:50]=2)=[CH:42][C:36]=1[O:37][CH2:38][C:39](O)=[O:40]>ClCCl.O>[CH3:1][C:2]1[C:7]2[N:8]=[C:9]([NH:11][C:39](=[O:40])[CH2:38][O:37][C:36]3[CH:42]=[C:43](/[CH:46]=[CH:47]/[C:48](=[O:61])[C:49]4[CH:50]=[C:51]([O:59][CH3:60])[C:52]([O:57][CH3:58])=[C:53]([O:55][CH3:56])[CH:54]=4)[CH:44]=[CH:45][C:35]=3[O:34][CH3:33])[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 151322-Amino-4-methylbenzothiazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 569681902-{2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxy phenyl)-1-propenyl]phenoxy}acetic acid

Produkt 1

HCID 60151529N1-(4-methyl-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxy phenyl)-1-propenyl]phenoxy}acetamideAusbeute 802 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-methyl-2-aminobenzothiazole (164 mg, 1.0 mmol) in dichloromethane (20 mL) was added 1-Ethyl-3-(3-Dimethylaminopropyl)carbodiimide (EDC) (191 mg, 1.0 mmol) and 1-hydroxy-1,2,3-benzotriazole (HOBt) (13.5 mg, 0.1 mmol). Then added 2-{2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxy phenyl)-1-propenyl]phenoxy}acetic acid (2) (402 mg, 0.1 mmol) and the reaction mixture was stirred at a temperature of 25° C. for 24 h and the reaction was monitored by TLC. Then to this water is added and extracted with dichloromethane. The solvent was evaporated under vacuum to afford the crude product. This was further purified by column chromatography using ethyl acetate and hexane as solvent system to obtain the pure product (9k) (440 mg, 80% yield)

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. customThe solvent was evaporated under vacuum
  3. customto afford the crude product
  4. customThis was further purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d417c5f001554fca95dba4525fa98a2b
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102638B2

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