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CAS No. : | 626-55-1 | MDL No. : | MFCD00006373 |
Formula : | C5H4BrN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NYPYPOZNGOXYSU-UHFFFAOYSA-N |
M.W : | 158.00 | Pubchem ID : | 12286 |
Synonyms : |
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Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | 1993 |
Hazard Statements: | H225-H302-H315-H319-H335 | Packing Group: | Ⅱ |
GHS Pictogram: |
* 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 |
---|---|---|
100% | Stage #1: at 30℃; for 0.0166667 h; Flow reactor Stage #2: With sodium hydroxide In N,N-dimethyl-formamide at 30℃; for 0.0433333 h; Flow reactor |
General procedure: All reactions were performed using a commercially available Vapourtec R-series set-up equipped with four pumps.(E)-Ethyl N-(mesitylsulfonyl)oxyacetimidate 7 was dissolved in MeCN (1M) and filtered. Perchloric acid (neat, 11.6M) was mixed with the first inlet via a Y-piece with flow rates of 1.228 mL/min and 0.106 mL/min respectively.Pyridine 2 was dissolved in MeCN (2M), filtered and introduced in a second Y-piece at flow rate 0.614 mL/min.Sodium hydroxide (1 M) was diluted with DMF to 0.667 M and introduced in a third Y-piece at flow rate 1.840mL/min. The stoichiometric ratio of all four inlets was 1:1:1:1. The system solvent was MeCN for the first threeinlets and H2O/DMF (2:1) for the fourth inlet. The PFA (polyfluoroalkoxy alkane polymer) reactor coils, withvolumes 20 mL, 2 mL and 10 mL respectively, were all set to temperature 30 °C. The reaction mixture from the firsttwo inlet streams spent 15 minutes residency time in the first reactor, the second 1.02 minutes and the third 2.64minutes.In all cases the power trace for the third reactor (where amination was occurring) showed that an exotherm took place(less power was required to heat to 30 °C). The operating pressure was 7-8 bar at beginning with just the first twopumps and rose to 9-10 bar with all 4 pumps. The reaction set-up was flushed afterwards with 33 percent aq. HCl (conc.)in MeOH followed by IPA. The total flow rate at the outlet was 3.788 mL/min.1-Amino-3-bromopyridin-1-ium 2,4,6-trimethylbenzenesulfonate (3a): The reaction was performed using generalflow procedure reacting 3-bromopyridine 2a with MSH 1. The outlet solution (25 mL, collected over 3.6 mins) wasconcentrated in vacuo to give an orange solid (3.6 mins collection time, >99percent). 1H NMR (400 MHz, d6-DMSO)2.18 (9H, s, 3 x CH3), 6.77 (2H, s, NH2), 7.93 (1H, dd, J = 4 and 8 Hz, ArH), 7.95 (s, 2H, ArH), 8.49 (1H, d, J = 8Hz, ArH), 8.81 (1H, d, J = 8 Hz, ArH), 9.17 (1H, s, ArH) ppm. 13C NMR (101 MHz, d6-DMSO) 20.3, 22.7, 121.4,128.6, 129.9, 135.8, 136.4, 138.6, 141.4, 142.5, 166.0 ppm. HRMS (FAB) calcd for C5H6BrN2+ 172.97144, found172.97105 and C9H11O3S- 199.04289 found 199.04277. DSC showed small exotherm with 61 J/g onset 249 °C andlarger exotherm with 573 J/g onset 299 °C. |