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[ CAS No. 343338-28-3 ]

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Chemical Structure| 343338-28-3
Chemical Structure| 343338-28-3
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Product Details of [ 343338-28-3 ]

CAS No. :343338-28-3 MDL No. :MFCD05861480
Formula : C4H11NOS Boiling Point : 220°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :121.20 g/mol Pubchem ID :11355477
Synonyms :

Safety of [ 343338-28-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 343338-28-3 ]

  • Upstream synthesis route of [ 343338-28-3 ]
  • Downstream synthetic route of [ 343338-28-3 ]

[ 343338-28-3 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 60011-16-7 ]
  • [ 343338-28-3 ]
YieldReaction ConditionsOperation in experiment
75% at -60 - 0℃; for 1 h; In the third step, 120 mL of diethoxymethane was added to the reaction flask, and the temperature was controlled between -60 °C and -70 °C. Liquid ammonia (23.8 g, 1.40 mol) was added dropwise to 2.6 mL of 2.3M n-hexyllithium (0.96). Molar), the solution appeared during the process of white solids, incubation reaction 0.5 hours. Then (S)-tert-butylsulfinyl tert-butyl thioester (169.8 g, 0.87 mol, 96.5percent ee) and ethyl chloride (80.4 g, 1.25 mol) were added dropwise to the diethoxymethane solution (by The product solution obtained in the second step was cooled to 0° C. and mixed with ethyl chloride). After the dropwise addition was completed, the reaction was incubated for 1 hour while the reaction was stirred and the reaction was completed. After the reaction solution was evaporated to dryness under reduced pressure, 1400 mL of methyl tert-butyl ether was added, filtered through celite, and the solvent was evaporated. 135 mL of n-heptane was slurried between -10°C and 0°C to obtain fine needle crystals. (3)-tert-butyl Sulfonamide 79.1 g, yield 75percent, HPLC: 99.7percent, 99.4percent ee.
Reference: [1] Patent: CN106478471, 2017, A, . Location in patent: Paragraph 0018; 0019
  • 2
  • [ 110-06-5 ]
  • [ 343338-28-3 ]
Reference: [1] Organic Letters, 2003, vol. 5, # 8, p. 1317 - 1320
  • 3
  • [ 861821-86-5 ]
  • [ 343338-28-3 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 26, p. 6386 - 6408
  • 4
  • [ 594836-47-2 ]
  • [ 108591-33-9 ]
  • [ 343338-28-3 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 26, p. 6386 - 6408
  • 5
  • [ 446021-65-4 ]
  • [ 343338-28-3 ]
Reference: [1] Journal of the American Chemical Society, 2002, vol. 124, # 27, p. 7880 - 7881
  • 6
  • [ 102191-92-4 ]
  • [ 343338-28-3 ]
  • [ 918413-70-4 ]
YieldReaction ConditionsOperation in experiment
94% With copper sulfate In dichloromethane at 20℃; for 48 h; A mixture of 2-(tert-butyldimethylsilyloxy)acetaldehyde (54.64 mL,258.2 mmol) in DCM (500 mL) was treated with (S)-2-methylpropane-2-sulfinamide (34.42 g, 284.0 mmol), followed by copper sulfate (103.0 g, 645.4 mmol) at ambient temperature. After stirring for 48 hours, the mixture was filtered through Celite and washed with DCM. The mixture was concentrated and purified on silica gel (10-30percent EtOAc in hexane) to provide (S,E)-N-(2-(tert-butyldimethylsilyloxy)ethylidene)-2-methylpropane-2-sulfinamide (67.3 g, 94percent yield).
61.7% With copper(II) sulfate In dichloromethane at 18 - 25℃; Intermediate 274: (S,E)-N-(2-^tert-butyldimethylsilyl)oxy)ethylidene)-2-methylpropane-2- sulfinamide To a solution of 2-((tert-butyldimethylsilyl)oxy)acetaldehyde (Aldrich, 15 g, 86.05 mmol) in DCM (200 mL) at room temperature was added copper(II) sulfate (41.2 g, 258.16 mmol) and (S)- 2-methylpropane-2-sulfinamide (Aldrich, 15.64 g, 129.08 mmol). The reaction mixture was stirred overnight at room temperature, then filtered through celite, washed with DCM and concentrated to afford an oil. Silica gel chromatography (0percent-25percent ethyl acetate/hexanes) afforded the title compound (14.73 g, 61.7percent) as a colorless oil. 1H NMR (300 MHz. CDC δ 0.11 (s, 6H), 0.93 (s, 9H), 1.22 (s, 9H), 4.55 (d, 2H), 8.07 (t, 1H).
Reference: [1] Patent: WO2011/29027, 2011, A1, . Location in patent: Page/Page column 121
[2] Chemistry - A European Journal, 2017, vol. 23, # 30, p. 7207 - 7211
[3] Journal of the American Chemical Society, 2007, vol. 129, # 3, p. 490 - 491
[4] Synthesis, 2007, # 8, p. 1235 - 1241
[5] Patent: WO2013/150296, 2013, A1, . Location in patent: Page/Page column 225
[6] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 5, p. 1607 - 1611
[7] Tetrahedron, 2016, vol. 72, # 32, p. 4968 - 4971
[8] Patent: WO2017/156179, 2017, A1, . Location in patent: Paragraph 00476; 00481; 00482
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