Structure of 62171-59-9
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 62171-59-9 |
Formula : | C10H13I |
M.W : | 260.11 |
SMILES Code : | IC1=CC=CC=C1C(C)(C)C |
MDL No. : | MFCD15527509 |
InChI Key : | MMFGMLZMUNVLHD-UHFFFAOYSA-N |
Pubchem ID : | 637957 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H319 |
Precautionary Statements: | P264-P280-P305+P351+P338-P337+P313 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | 2-t-Butylaniline (13.35 g, 89.4 mmol) was diazotized in sulfuric acid (25% w/w, 110 mL) with sodium nitrite (9.34 g) in water (18 mL) at -20 C. The diazonium salt was transferred to a solution of potassium iodide (67 g) in water 20 mL, and after 18 hours, a solution of sodium hydroxide (25 g) in water (100 mL) was added. The mixture was extracted with hexanes, hexane extracts passed through a column of silica gel, and concentrated. The product was obtained as a liquid, 13.77 g (59%). Mass spec: m/z 260 (M+). 1H NMR (CDCl3) δ ppm: 1.53 (s, 9H), 6.82 (td, 1H, 1.68 and 7.68 Hz), 7.27 (td, 1H, 1.4 and 7.32 Hz), 7.43 (dd, 1H, 1.64 and 8.0 Hz), 7.99 (dd, 1.4 and 7.8 Hz). | |
45% | With toluene-4-sulfonic acid; potassium iodide; sodium nitrite; In water; tert-butyl alcohol; at -3 - 20℃; for 17.5h; | 28.7g (151mmol) of p-toluenesulfonic acid monohydrate were dissolved in 75ml of tert- butanol.5.0g (33.5mmol) of 2-(tert-butyl)aniline were added, and the final white suspension was cooled to -3C. A solution of 6.93g (101mmol) of sodium nitrite and 20.86g (126mmol) of potassium iodide in 30ml of water was added within 30 minutes. It was warmed up to room temperature and stirred for 17 hours.27.4g (174mmol) of sodium sulfurothioate were dissolved in 100ml of water and added to the reaction mixture.11.26g (134mmol) of sodium bicarbonate were dissolved in 100ml of water and added, then the mixture was stirred for 30 minutes. The reaction mixture was diluted with 200ml of cyclohexane, the phases were separated and the water phase was extracted with cyclohexane. The combined organic phases were washed with water and brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The crude product was purified by column chromatography (heptane/ethyl acetate) to give 5.36g (45% yield) of Intermediate 47-1. 1H NMR (400 MHz, Methylene Chloride-d2) d 8.00 (dd, J = 7.8, 1.5 Hz, 1H), 7.46 (dd, J = 8.0, 1.7 Hz, 1H), 7.36- 7.23 (m, 1H), 6.89- 6.78 (m, 1H), 1.54 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | 11.8g (45.4 mmol) of Intermediate 47-1 were dissolved in 60ml of tetrahydrofuran. The orange solution was bubbled with argon and cooled to -78C.18.48ml (49.9mmol) of n- butyllithium (2.7M in pentane) were added slowly and the reaction mixture was stirred for 30 minutes.3.86ml (49.9mmol) of N,N-dimethylformamide were added at -78C and stirred for 30 minutes at this temperature, then it was heated up to room temperature and stirred for 18 hours.100ml of water and 100ml of heptane were added, the phases were separated and the water phase was extracted with heptane. The combined organic phases were washed with water and brine, dried over magnesium sulfate, filtered and concentrated under vacuum to give 9.24g (86% yield) of Intermediate 47-2. 1H NMR (300 MHz, Methylene Chloride-d2) d 10.83 (d, J = 0.9 Hz, 1H), 7.89 (dt, J = 7.6, 1.1 Hz, 1H), 7.58- 7.44 (m, 2H), 7.40- 7.23 (m, 1H), 1.52 (s, 9H). |