N,N-Dimethylcyclohexylamine → HCID 178446290, Verbindung

HRID 1066123

Reaktionsgleichung

Reaktionsgleichung von HRID 1066123
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CN(C1CCCCC1)C.Cl.[CH3:25][CH:26]([NH2:30])[CH:27]([CH3:29])[CH3:28].[Cl:31][C:32]1[CH:33]=[CH:34][C:35]2[S:40](=[O:42])(=[O:41])[NH:39][C:38](=O)[NH:37][C:36]=2[CH:44]=1>O>[Cl:31][C:32]1[CH:33]=[CH:34][C:35]2[S:40](=[O:42])(=[O:41])[N:39]=[C:38]([NH:30][CH:26]([CH3:25])[CH:27]([CH3:29])[CH3:28])[NH:37][C:36]=2[CH:44]=1

Komponenten

6

Edukt 4

HCID 7415N,N-DimethylcyclohexylamineHCID 14812Phosphorus oxide (P4O10)HCID 1207933-Methylbutan-2-amine--hydrogen chloride (1/1)HCID 124870946-chloro-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

Produkt 1

HCID 178446290HCID 178446290, VerbindungAusbeute 37,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
195 °C

Versuchsvorschrift

Phosphorus pentoxide (7.55 g, 53.2 mmol), N,N-dimethylcyclohexylamine (17 ml, 113 mmol) and 1,2-dimethylpropylamine hydrochloride (12.4 g, 100.4 mmol) were carefully mixed and heated with mechanical stirring on an oil bath at 190-200° C. for about 15 min. To the homogeneous mass was added 6-chloro-3,4-dihydro-3-oxo-1,2,4-benzothiadiazine 1,1-dioxide (5.84 g, 25.1 mmol) and the mixture was stirred at 235° C. for 2 h. After cooling to about 100° C., water (200 ml) was added and the dark mixture was hydrolysed by stirring over night at room temperature. The precipitate was isolated by filtration and recrystallised from ethanol with decolorising charcoal to give 2,83 g (37%) of the pure title compound; m.p. (DSC) 264.7° C.; 1H-NMR (DMSO-d6): δ 0.90 (dd, 6H, CH(CH3)2), 1.09 (d, 3H, NCHCH3), 1.76 (m, 1H, CH(CH3)2), 3.70 (m, 1H, NHCH), 7.15 (br., 1H, NH), 7.28 (m, 2H, ArH), 7.68 (d, 1H, ArH), 10.3 (br.s, 1H, NH); (C12H16N3Cl1O2S1) calc. C, 47.76; H, 5.34; N 13.92; found C, 47.66; H, 5.47; N, 13.91.

Aufarbeitung

  1. temperatureheated
  2. stirringthe mixture was stirred at 235° C. for 2 h
  3. temperatureAfter cooling to about 100° C.
  4. stirringby stirring over night at room temperature
  5. customThe precipitate was isolated by filtration
  6. customrecrystallised from ethanol with decolorising charcoal

Quellen und Nachweise

ORD-Eintrag
ord-f016c12d72c64a0585f8931cb1a8c3fa
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06242443B1

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