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[ CAS No. 2512-24-5 ]

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Chemical Structure| 2512-24-5
Chemical Structure| 2512-24-5
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CAS No. :2512-24-5 MDL No. :MFCD00462465
Formula : C10H15NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :213.30 g/mol Pubchem ID :314059
Synonyms :

Safety of [ 2512-24-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2512-24-5 ]

  • Upstream synthesis route of [ 2512-24-5 ]
  • Downstream synthetic route of [ 2512-24-5 ]

[ 2512-24-5 ] Synthesis Path-Upstream   1~3

  • 1
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  • [ 150691-04-6 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5 h;
Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at 20℃; for 3.5 h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane at 20℃;
To a solution of the compound of example 3 (15.92 g, 74.7 mmol) in tetrahydrofuran (200 ml) in an ice bath was added 1.6M n-butyllithium in hexane (100 ml, 164 mmol) dropwise over 30 minutes. The mixture remained a clear solution. In an ice bath it was added triisopropylborate (24.1 ml, 104 mmol) dropwise. The mixture was stirred at room temperature for 3.5 hrs, solution becoming cloudy. After it was cooled in an ice bath, 1N hydrochloride (200 ml) was added. The mixture was stirred at room temperature overnight. It was extracted with ether (2.x.50 ml). The organic extract was washed with 1N sodium hydroxide (2.x.60 ml). The aqueous solution was acidified to pH=1 with 6N hydrochloride, and then extracted with ether (2.x.100 ml). The ether extract was dried over magnesium sulfate, and concentrated in vacuo. The crude product was recrystallized by ether and hexane to give the title compound as a while solid (11.5 g, 60percent). ES-MS (M+H)+=258.
60%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at 0 - 2℃; for 0.583333 h;
Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at 35℃; for 1 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water for 0.5 h;
Part A.
Preparation of 2-(t-butylamino)sulfonylphenylboronic acid
To a solution of 34.0 g (0.16 mol) of benzene-N-(t-butylsulfonamide in 500 ML of THF under N2 was added 160 ML (0.36 mol) of 2.25M n-butyllithium in hexane over 35 min, keeping the temperature between 0°-2°C.
The reaction mixture was allowed to warm to room temperature over 1.5h, during which time a thick precipitate formed..
triisopropylborate (46 ML, 0.20 mol) was added, keeping the temperature below 35°C.
After 1h, the reaction mixture was cooled, 1N HCl (260 ML) was added, and the mixture was stirred for 30 min..
After diluted with 520 ML of water, the mixture was extracted with 3x400 ML of ether..
The combined organic extracts were extracted with 3x250 ML of 1N NaOH.
The aqueous extracts were acidified to PH 1 with 6N HCl, and then extracted with 3x250 ML of ether..
The ether extracts were washed with 250 ML of brine, dried over MgSO4, and the solvents were removed in vacuo to yield 45 g of a thick oil..
After addition of toluene (45 ML), the mixture was agitated for 1h on the rotary evaporator..
A small quantity of solid formed, which was used to induce partial solidification of the remaining crude product..
Addition toluene (150 ML) was added, and the mixture was reduced to 1/2 volume in vacuo, keeping the temperature from 0°-10°C.
The resulting precipitate was collected and washed with hexane, then dried under vacuum to give 24.6 g (60percent) of the title compound as white crystals. m.p. 118°-119°C.1HNMR (CDCl3): d 1.18 (s, 9H); 5.13 (s, 1H); 6.29 (br s, 2H); 7.53 (m, 2H); 7.82 (d, 1H); 8.00 (d, 1H).
Reference: [1] Patent: US6673817, 2004, B1, . Location in patent: Page column 200
[2] Patent: EP874629, 2004, B1, . Location in patent: Page/Page column 15-16
[3] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 22, p. 2947 - 2950
[4] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 12, p. 1651 - 1655
[5] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 14, p. 6841 - 6849
[6] Patent: WO2006/63293, 2006, A2, . Location in patent: Page/Page column 45
[7] Patent: US2012/245144, 2012, A1, . Location in patent: Page/Page column 133
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  • [ 150691-04-6 ]
Reference: [1] Patent: US2003/65176, 2003, A1,
[2] Patent: US6399627, 2002, B1,
[3] Patent: US6399627, 2002, B1,
[4] Patent: US5436259, 1995, A,
[5] Patent: EP1443041, 2004, A1, . Location in patent: Page 24
  • 3
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  • [ 150691-04-6 ]
YieldReaction ConditionsOperation in experiment
42%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -5 - 22℃; for 1 h; Inert atmosphere
Stage #2: at -5 - 22℃; for 3 h;
Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water
Step 2: 2-Borono-N-tert-butylbenzenesulfonamide; 27 ml of n-butyllithium (15percent solution in n-hexane) are added dropwise at -5° C. to a solution of 4.29 g of N-tert-butylbenzenesulfonamide in 25 ml of THF under argon. The mixture is stirred at 22° C. for 1 h, re-cooled to -5° C., and 2.8 g of trimethyl borate are slowly added dropwise. The mixture is stirred at 22° C. for 3 h, before 100 ml of aqueous ammonium chloride solution is added dropwise. The phases are separated, and the aqueous phase is extracted a further twice with MTB ether. The combined organic phases are dried over magnesium sulfate. Filtered and evaporated to dryness in vacuo.Yield: 42percent of 2-borono-N-tert-butylbenzenesulfonamide;HPLC retention time: 2.42 min (method 2).
Reference: [1] Patent: US2011/245225, 2011, A1, . Location in patent: Page/Page column 41
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