N,N-Dimethylcyclohexylamine → HCID 178446290, compound

HRID 1066123Notes

Reaction equation

HRID 1066123 reaction equation
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

Participants

6

Reactant 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

Product 1

HCID 178446290HCID 178446290, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
195 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f016c12d72c64a0585f8931cb1a8c3fa
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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