N,N-Dimethylcyclohexylamine → HCID 178446290、化合物

HRID 1066123

反応式

HRID 1066123 の反応式
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

参加物

6

反応物 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

生成物 1

HCID 178446290HCID 178446290、化合物収率 37.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
195 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f016c12d72c64a0585f8931cb1a8c3fa
出典データセット
uspto-grants-2001_06
特許番号
US06242443B1

関連ノート

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