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Structure of 88-10-8
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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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CAS No. : | 88-10-8 |
Formula : | C5H10ClNO |
M.W : | 135.59 |
SMILES Code : | O=C(Cl)N(CC)CC |
MDL No. : | MFCD00000636 |
InChI Key : | OFCCYDUUBNUJIB-UHFFFAOYSA-N |
Pubchem ID : | 6916 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H227-H290-H302-H314-H332-H351 |
Precautionary Statements: | P264-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P363-P405-P501 |
Class: | 8 |
UN#: | 3265 |
Packing Group: | Ⅲ |
* 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 |
---|---|---|
2.4 g (82%) | In tetrahydrofuran; | EXAMPLE 4 1(2 or 3)-N,N-Diethylcarbamyl-<strong>[15294-81-2]4,5-dibromo-1H-1,2,3-triazole</strong> STR13 To a suspension of 213 milligrams (mg) (8.89 mmoles) of sodium hydride in 20 ml of anhydrous tetrahydrofuran was added 2 g (8.89 mmoles) of <strong>[15294-81-2]4,5-dibromo-1H-1,2,3-triazole</strong>. The resulting suspension was cooled to 0° C. and 1.2 g (8.89 moles) of N,N-diethylcarbamoyl chloride was added by drop. The reaction mixture was heated to reflux overnight and the precipitated sodium chloride was removed by filtration. Concentration of the filtrate in vacuo gave 2.4 g (82percent) of 1(2 or 3)-N,N-diethylcarbamyl-<strong>[15294-81-2]4,5-dibromo-1H-1,2,3-triazole</strong> as a yellow oil. The structure was confirmed by n.m.r. and I.R. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.5% | With triethylamine; at 20℃; for 0.333333h; | 136 g ( 1 Mole) of m-toluic acid (3-methyl benzoic acid) and 136 g (= 1 27 ml. 1 Mole) N,N-diethylcarbamoyl chloride are taken in a 1 liter two-necked round-bottom flask lltted with air condenser which is placed over a magnetic stirrer. To this, 121 g ( 167 ml. 1.2 Mole) of triethylamine, which is a organic base is added using a pressure-equalizing funnel fitted in the side neck of the round bottom flask at room temperature. After complete addition, the reaction m ixture is stirred constantly for 20 minutes at room temperature. The reaction mixture is then treated with 250 ml of water and the two layers are separated. Pure and colourless N,N-diethyl m-toluamide (DEET) is obtained by vacuum disti l lation of organic layer wh ich is the product. Purity of the compound is analyzed using GC-MS which is more than 99.5%. The yield of the product is 186 g (97.5%). |
97.5% | With triethylamine; at 20℃; for 0.333333h; | Example 2 Preparation of N,N-Diethyl m-Toluamide (DEET) [0095] 136 g (1 Mole) of m-toluic acid (3-methyl benzoic acid) and 136 g (=127 ml, 1 Mole) N,N-diethylcarbamoyl chloride are taken in a 1 liter two-necked round-bottom flask fitted with air condenser which is placed over a magnetic stirrer. To this, 121 g (167 ml. 1.2 Mole) of triethylamine, which is a organic base is added using a pressure-equalizing funnel fitted in the side neck of the round bottom flask at room temperature. After complete addition, the reaction mixture is stirred constantly for 20 minutes at room temperature. The reaction mixture is then treated with 250 ml of water and the two layers are separated. Pure and colourless N,N-Diethyl m-toluamide (DEET) is obtained by vacuum distillation of organic layer which is the product. [0096] Purity of the compound is analyzed using GC-MS which is more than 99.5%. The yield of the product is 186 g (97.5%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With pyridine; at 90℃; for 2h; | N,N-diethyl-4.(pyridln-3-yl)-1 H-imldazole-1 -carboxamideCharge 3-(IH-imidazol-4-yl)pyridine (0.5 g, 3.44 mmcl) and Pyridine (2.5 ml). Charge diethylcarbamic chloride (0.467 g, 3.44 mmcl).The reaction mixture was heated to 90C and stir for lhr.Sample for TLC. Still starting material, more carbamoyl chloride (0.3g) was added. The mixture was stirred for lh and the reaction conversion was checked by TLC (DCM/MeOH, 9:1). No starting material left.The reaction was cooled to room temperature and the pyridine was removed.The mixture was diluted with sat NaHCO3 and DCM. The biphasic mixture was separated. The aqueous layer was washed with DCM.The combined organic layers were washed with sat NaHCO3, dried over Na2SO4, concentrated to dryness.Yellow oil (0. 835mg) was obtained in 94% molar yield; purity >95%1C NMR (150 MHz, CDCI3, 20C) 6: 150.8, 148,5, 146.7, 139.3, 137, 132.4, 129, 123.6, 113.8,42.8, 13.2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20%; 37% | With pyridine; In toluene; at 20℃; for 48h; | Example 45 (Synthesis of (S)-2-((R)-4-(diethylcarbamoyloxy)-3-hydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl palmitate (Compound 1-244) and (S)-2-((R)-3,4-bis(diethylcarbamoyloxy)-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl palmitate (Compound 1-246)) First, 6-O-palmitoyl-L-ascorbic acid (2.00 g, 4.82 mmol) was dissolved in pyridine (15 mL), and the resulting solution was cooled in an ice bath containing added salt. A toluene solution (5 mL) containing diethylcarbamoyl chloride (0.70 g, 5.16 mmol) was then added dropwise. The temperature of the reaction solution was then gradually raised to room temperature, and the reaction was allowed to proceed at the same temperature for two days. Subsequently, the insoluble material was removed by filtration and washed with toluene. The filtrate was then concentrated, and the residue was purified by silica gel column chromatography, yielding (S)-2-((R)-4-(diethylcarbamoyloxy)-3-hydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl palmitate (compound 1-244) in an amount of 0.50 g, a yield of 37%, and (S)-2-((R)-3,4-bis(diethylcarbamoyloxy)-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl palmitate (compound 1-246) in an amount of 0.12 g, a yield of 20%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With dmap; In dichloromethane; at 0 - 20℃;Inert atmosphere; | General procedure: Acyl chloride (0.18 mmol, 1.1 eq) was added at 0 C to a solution of <strong>[436-77-1]fangchinoline</strong> (100 mg, 0.16 mmol) and DMAP (0.032 mmol, 0.2eq) in 2 mL dry CH2Cl2 under argon and stirred for 2-4 h. The reaction mixture was quenched with a saturated aqueous solution of sodium bicarbonate and extracted three times with CH2Cl2. The combined organic phase was dried over anhydrous magnesium sulfate before vacuum suction filtration. The removal of the solventin vacuo afforded the crude product, which was chromatographied on silica gel (CH2Cl2/MeOH, 50/1 v/v, 0.1% TEA) to provide the pureproduct 1a-1e, 2a-2g, 3a-3e and 4a-4h. |