Water → 2-(1-Amino-1-methylethyl)-4,5-bis(4-methoxyphenyl)thiazole hydrochloride

HRID 483975Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 483975
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[Cl:11])=[CH:5][CH:4]=1.C(OC([NH:28][C:29]([CH3:34])([CH3:33])[C:30](=[S:32])[NH2:31])=O)(C)(C)C.O>CN(C)C=O>[ClH:11].[NH2:28][C:29]([C:30]1[S:32][C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:31]=1)([CH3:34])[CH3:33]

Komponenten

5

Edukt 3

HCID 962WaterHCID 38625232-Chloro-1,2-bis(4-methoxyphenyl)ethan-1-oneHCID 15186362tert-butyl N-(1-carbamothioyl-1-methylethyl)carbamate

Produkt 1

HCID 197489022-(1-Amino-1-methylethyl)-4,5-bis(4-methoxyphenyl)thiazole hydrochlorideAusbeute 81,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 1,2-bis(4-methoxyphenyl)-2-chloroethanone (5.00 g) and 2-tert-butyloxycarbonylamino-2-methylpropanethioamide (4.50 g) in dimethylformamide (25 ml) was stirred at 70° C. for 6 hours. After allowing to cool to the ambient temperature, the reaction mixture was dropped into water. The precipitates were collected by filtration. The resulting residue (6.28 g) was dissolved with dichloromethane (120 ml), and stirred at 2° C. To the reaction mixture was added 1,4-dioxan solution of 4N hydrogen chloride (60 ml), and stirred at ambient temperature for 1 hour. The resulting residue was evaporated in vacuo. The residue was added iso-propyl ether (300 ml) and stirred at 2° C. for 3 hours. The resulting precipitate was collected by filtration and washed with iso-propyl ether, to give 2-(1-amino-1-methylethyl)-4,5-bis(4-methoxyphenyl)thiazole hydrochloride (5.5 g).

Aufarbeitung

  1. temperatureto cool to the ambient temperature
  2. filtrationThe precipitates were collected by filtration
  3. dissolutionThe resulting residue (6.28 g) was dissolved with dichloromethane (120 ml)
  4. stirringstirred at 2° C
  5. additionTo the reaction mixture was added 1,4-dioxan solution of 4N hydrogen chloride (60 ml)
  6. stirringstirred at ambient temperature for 1 hour
  7. customThe resulting residue was evaporated in vacuo
  8. additionThe residue was added iso-propyl ether (300 ml)
  9. stirringstirred at 2° C. for 3 hours
  10. filtrationThe resulting precipitate was collected by filtration
  11. washwashed with iso-propyl ether

Quellen und Nachweise

ORD-Eintrag
ord-c0b22498621a4c2cbe4b8f6c1dc95c8a
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05229386

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