N,N-Dimethylcyclohexylamine → HCID 178446290, 화합물

HRID 1066123

반응식

HRID 1066123 반응식
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

참가 물질

6

반응물 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

생성물 1

HCID 178446290HCID 178446290, 화합물수율 37.4%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
195 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f016c12d72c64a0585f8931cb1a8c3fa
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06242443B1

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