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Chemical Structure| 72597-34-3 Chemical Structure| 72597-34-3

Structure of 72597-34-3

Chemical Structure| 72597-34-3

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Product Details of [ 72597-34-3 ]

CAS No. :72597-34-3
Formula : C10H17NO3S
M.W : 231.31
SMILES Code : O=C(CC(C(C)1C)CC2)[C@@]21CS(=O)(N)=O
MDL No. :MFCD00151500

Safety of [ 72597-34-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 72597-34-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 72597-34-3 ]
  • Downstream synthetic route of [ 72597-34-3 ]

[ 72597-34-3 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 72597-34-3 ]
  • [ 107869-45-4 ]
YieldReaction ConditionsOperation in experiment
92% With Amberlyst H+ resin In toluene for 4 h; Heating / reflux EXAMPLE 1; (1R)-(+)-2,10-Camphor Sultam (Scheme 3, 3-1); To a solution of (-) camphor sulfonic acid (1.45 kg, 6.25 mol) in chloroform (7 L) under reflux condition is added thionyl chloride (0.896 kg, 7.5 mol) over a period of 1 h. The reaction mixture is refluxed for 16 h and then cooled to 4° C. using an ice bath. This cooled reaction mixture is added slowly to conc. NH4OH (15 L) while maintaining the temperature below 15° C. during the addition. After addition, the mixture is stirred for 4 h at room temperature. The organic layer is separated and the aqueous layer is extracted with chloroform (2.x.2 L). The combined organic extracts are washed with brine (4 L) and dried over MgSO4. After filtration, the filtrate is concentrated under vacuum and dried to give 1.2 kg (83percent) of camphor sulfonamide. In one experiment at 145 g scale of camphor sulfonic acid, the use of dichloromethane instead of chloroform for the reaction and extraction gives comparable yields. To a suspension of the camphor sulfonamide (1.2 kg, 5.2 mol) in toluene (15 L) is added Amberlyst H+ resin (150 g), and the mixture is heated at reflux for 4 h with the water formed removed azeotropically using a Dean-Stark water separator. The reaction mixture is filtered hot to remove the resin. The filtrate on cooling gave a white solid which is collected by filtration to give 1.02 kg (92percent) of the desired imine. To the above imine (100 g, 0.47 mol) in ethanol (0.75 L) is added Raney Nickel (100 g) and the mixture is hydrogenated at 40 psi for 2 h. The catalyst is removed by filtration and the filtrate concentrated under vacuum to give the product 3-1 as a white solid
References: [1] Tetrahedron, 1986, vol. 42, # 14, p. 4035 - 4044.
[2] Chemical Communications, 1998, # 15, p. 1549 - 1550.
[3] Journal of the American Chemical Society, 1988, vol. 110, p. 8477.
[4] Patent: US2006/128789, 2006, A1, . Location in patent: Page/Page column 7.
[5] Organic Process Research and Development, 2005, vol. 9, # 2, p. 193 - 197.
[6] Organic Syntheses, 1990, vol. 69, p. 158 - 158.
 

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