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CAS No. : | 38460-95-6 | MDL No. : | MFCD00000772 |
Formula : | C11H19ClO | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | MZFGYVZYLMNXGL-UHFFFAOYSA-N |
M.W : | 202.72 | Pubchem ID : | 38042 |
Synonyms : |
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Chemical Name : | 10-Undecenoylchloride |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 3265 |
Hazard Statements: | H314 | 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 |
---|---|---|
2.68 Parts of <strong>[3325-11-9]5-aminobenzotriazole</strong> (prepared as described in U..S. Pat. No. 4,428,987) were reacted with 7.5 parts of undec-10-enoyl chloride (prepared as described in part A), using the procedure described in Example 4 for the preparation of 6(octadec-9,12-dienoylamino)-2-mercaptobenzothiazole. The product (4.5 parts, melting point 189°-191° C., 73.3percent yield) was found by analysis to contain C 66.5percent wt; H 8.4percent wt; and N 17.8percent wt. 5(undec-10-enoylamino)-benzotriazole (C17 H24 N4 O) requires C 68percent wt; H 8.0percent wt; and N 18.7percent wt. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With pyridine; In diethyl ether; for 2h;Reflux; | Step 1: Synthesis of 10-amidoundec-1-eneiminodiacetic acid methyl ester Added to a solution of dimethyliminodiacetate (hydrochloride) (3.08 g; 16 mmol) dissolved in 50 ml of anhydrous ether was pyridine (2.46 g; 2.59 ml; 35 mmol; 2 eq.). The solution was heated under reflux of ether and the undecenoyl chloride (97%) (3.48 g, 3.7 ml, 17 mmol, 1 eq.) was added very slowly (approximately over a period of one hour). The reaction was continued under reflux of ether for 1 hour. The reaction mixture was filtered, then the filtrate was concentrated to give a residue which was then purified by chromatography over silica gel (cyclohexane?cyclohexane/ethyl acetate (70/30)) to give a white solid. The characteristics of the product obtained were the following: Mass obtained: 3.85 g Yield: 74% 1H NMR (200 MHz; CDCl3): 1.30 (10H; m; H7-11); 1.64 (2H; m; H6); 2.03 (2H; m; H12); 2.30 (2H; t; H5; JH-H=7.4 Hz); 3.72 (3H; s; H1); 3.77 (3H; s; H1); 4.16 (2H; s; H3); 4.19 (2H; s; H3); 4.96 (2H; m; H14); 5.81 (1H; m; H13) 13C NMR (200 MHz; CDCl3): 25.18 (C6); 29.28; 29.45; 29.59; 29.69; 29.74; 33.06 (C5); 34.18 (C12); 48.18 (C3); 50.34 (C3); 52.53 (C1); 52.90 (C1); 114.52 (C14); 139.58 (C13); 169.88 (C2); 170.30 (C2); 174.02 (C4) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | 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. |