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CAS No. : | 64205-92-1 | MDL No. : | MFCD03426388 |
Formula : | C3H6N2O3S | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | JTRHTNVGGLWMFV-UHFFFAOYSA-N |
M.W : | 150.16 | Pubchem ID : | 274561 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | |
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 |
---|---|---|
Pd-C; In methanol; methanolic ammonia; ethanol; 2-methyl-propan-1-ol; chloroform; | Example 15 (5R),(8S)-2-(5,6,7,8-Tetrahydro-8-isopropyl-5-methyl-quinolin-3-yl)amino-2-imidazoline (5R), (8S)-3-Amino-5,6,7,8-tetrahydro-8-isopropyl-5-methylquinoline. (-)-Menthone (390 mg, 2.53 mm(1) was mixed with 1-methyl-3,5-dinitro-2-pyridone (500 mg, 2.51 mmol) in 1M methanolic ammonia (50 mL, 50 mmol) and heated at reflux overnight. The solvent was evaporated off and the residue was dissolved in CHCl3 and flash chromatographed over silica gel (37 g) eluding with EtOAc/hexane (1:20) to afford a colorless oil (248 mg, 1.06 mmol). It was dissolved in MeOH (5 mL), treated with 10% Pd-C (27 mg) and hydrogenated at 1 atm for 2 h. Filtration through Celite gave a pale yellow solid (207 mg). It was partitioned between CH2 Cl2 and 2N HCl. The organic layer was further extracted with 2N HCl before the aqueous layer was basined with Na2 CO3 solution and extracted with CH2 Cl2 to afford a white solid (123 mg, 24% yield). (5R), (8S)-2-(5,6,7,8-Tetrahydro-8-isopropy-5-methyl-quinolin-3-yl)amino-2-imidazoline. The above amine (119 mg, 0.58 mmol) was mixed with 2-imidazolinesulfonic acid (180 mg, 1.20 mmol) in isobutyl alcohol (5 mL) aid heated at reflux for 2 days. The solvent was evaporated off to give a residue which was dissolved in CHCl3 and flash chromatographed over silica gel (17 g) eluding with EtOAc/MeOH/Et3 N (20:3:1) to afford a white solid (129 mg, 81% yield). It was dissolved in EtOH and reated with fumaric acid (110 mg) in EtOH. Upon addition of ether and refrigeration, the solution gave white crystals (43 mg): mp 151-154 C. Anal. Calcd. for C16 H24 N4.1.6C4 H4 O4: C, 58.73; H, 6.69; N, 12.23. Found: C, 58.41; H, 7.04; N, 12.24. |
[ 1184-90-3 ]
Amino(imino)methanesulfonic acid
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