Structure of 3119-15-1
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CAS No. : | 3119-15-1 |
Formula : | C7H4I3NO2 |
M.W : | 514.83 |
SMILES Code : | O=C(O)C1=C(I)C=C(I)C(N)=C1I |
MDL No. : | MFCD00007681 |
InChI Key : | QMQFFHSJUJDRPG-UHFFFAOYSA-N |
Pubchem ID : | 18387 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302+H312+H332-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312+P330-P305+P351+P338 |
* 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 |
---|---|---|
79% | In 2,4-dichlorophenoxyacetic acid dimethylamine; | A 3-[(2-chloroacetyl)amino]-2,4,6-triiodobenzoic acid According to the procedure described in Example 1, a suspension of 103 g of <strong>[3119-15-1]3-amino-2,4,6-triiodobenzoic acid</strong> (Beil. XIV, 414) (0.2 mol) in 200 ml of DMA is added to 24.8 g of chloroacetyl chloride (0.22 mol). 93.27 g of 3-[(2-chloroacetyl)amino]-2,4,6-triiodobenzoic acid are obtained (0.158 mol). Yield: 79% m.p.: 253-255 C. TLC: silica gel plate 60F 254 Merck. Eluent: CHCl3: MeOH: NH4 OH 25%=4:4:2. Detector: UV light (254 nm) Rf=0.69. 1 H-NMR, 13 C-NMR, IR and MS spectra are consistent with the assigned structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; In water; 2,4-dichlorophenoxyacetic acid dimethylamine; | A 3-[6-[(chloroacetyl)amino]-1-oxohexyl]amino-2,4,6-triiodobenzoic acid To 207.6 g of 6-[(chloroacetyl)amino]hexanoic acid (prepared according to the procedure described in J. Chromatography 1984, 292, 369-382) (1.00 mol), 305.4 g of thionyl chloride (2.57 mol) are slowly added and the reaction mixture heated at 60 C. After 3 h, the thionyl chloride in excess is removed. The residue is dropwise added to a suspension of 360.7 g of <strong>[3119-15-1]3-amino-2,4,6-triiodobenzoic acid</strong> (Beil. XIV, 414) (0.70 mol) in 600 ml of DMA, and leaving the temperature to rise up to 55 C. The temperature is adjusted to 60 C. and maintained for 2 h. The resulting solution is poured in 6 l of H2 O and ice obtaining a precipitate which is filtered. The residue is dissolved in 2 l of methyl ethyl ketone, the solution is concentrated, and after germination, the desired product precipitates. 212.3 g of 3-[6-[(chloroacetyl)amino]-i-oxohexyl]amino-2,4,6-triiodobenzoic acid (0.30 mol) are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In N,N-dimethyl-formamide; at 60℃; for 5.0h; | Then, 0.357 g (1 mmol) of the DTPA anhydride was added to 30 ml of anhydrous dimethylformamide (DMF), and mixed with stirring. This solution was supplemented with 0.515 g (1 mmol) of <strong>[3119-15-1]3-amino-2,4,6-triiodobenzoic acid</strong>, and allowed to react at 60C for 5 hrs with stirring. After the reaction was completed, the solvent was removed under pressure using an evaporator, and the remaining material was washed with ethanol and dried, thereby obtaining the desired product at a yield of 80%. 1H NMR (D2O+NaOD, ppm) 2.36 (m, 8H, CH2CH2), 2.80~2.90 (d, 10H, CH2CO), 7.95 (s, 1H, Ar-H); 13C NMR (D2O+NaOD, ppm) 37.03, 52.05, 52.18, 58.89, 59.32, 74.93, 77.83, 80.44, 147.58, 153.27, 171.43, 180.04, 180.18; IR (cm-1) 3433, 1730, 1634, 1517, 1243. |
80% | In N,N-dimethyl-formamide; at 60℃; for 5.0h; | 10.0 g (25 mmol) of DTPA was dispersed in 20 ml of pyridine. 18 g (0.18 mol) of acetic anhydride was added to the dispersion, and a reaction was allowed to take place at 65 for 24 hrs with stirring. After the reaction was completed, the reaction mixture was filtered to recover generated material. The recovered compound was washed with acetic anhydride and diethyl ether several times, and dried under pressure for 24 hrs, thereby obtaining a DTPA anhydride at a yield of 78%. IR(cm-1) 2979, 1820, 1774, 1641. Then, 0.357 g (1 mmol) of the DTPA anhydride was added to 30 ml of anhydrous dimethylformamide (DMF), and mixed with stirring. This solution was supplemented with 0.515 g (1 mmol) of <strong>[3119-15-1]3-amino-2,4,6-triiodobenzoic acid</strong>, and allowed to react at 60 for 5 hrs with stirring. After the reaction was completed, the solvent was removed under pressure using an evaporator, and the remaining material was washed with ethanol and dried, thereby obtaining the desired product at a yield of 80%. 1H NMR (D2O+NaOD, ppm) 2.36 (m, 8H, CH2CH2), 2.802.90 (d, 10H, CH2CO), 7.95 (s, 1H, Ar-H); 13C NMR (D2O+NaOD, ppm) 37.03, 52.05, 52.18, 58.89, 59.32, 74.93, 77.83, 80.44, 147.58, 153.27, 171.43, 180.04, 180.18; IR (cm-1) 3433, 1730, 1634, 1517, 1243. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In N,N-dimethyl-formamide; at 60℃; for 5.0h; | 0.357 g (1 mmol) of the DTPA anhydride was added to 30 ml of anhydrous dimethylformamide (DMF), and mixed with stirring. This solution was supplemented with 0.13 g (2 mmol) of <strong>[3119-15-1]3-amino-2,4,6-triiodobenzoic acid</strong>, and allowed to react at 60C for 5 hrs with stirring. After the reaction was completed, the solvent was removed under pressure using an evaporator, and the remaining material was washed with ethanol and dried, thereby obtaining the desired product at a yield of 75%. 1H NMR (D2O+NaOD, ppm) 2.34 m, 8H, CH2CH2), 2.78~2.86 (d, 10H, CH2CO), 7.92 (s, 2H, Ar-H). |
75% | In N,N-dimethyl-formamide; at 60℃; for 5.0h; | 0.357 g (1 mmol) of the DTPA anhydride was added to 30 ml of anhydrous dimethylformamide (DMF), and mixed with stirring. This solution was supplemented with 0.13 g (2 mmol) of <strong>[3119-15-1]3-amino-2,4,6-triiodobenzoic acid</strong>, and allowed to react at 60 for 5 hrs with stirring. After the reaction was completed, the solvent was removed under pressure using an evaporator, and the remaining material was washed with ethanol and dried, thereby obtaining the desired product at a yield of 75%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide; sulfuric acid;copper(I) chloride; In water; | EXAMPLE 3 20.6 g. of <strong>[3119-15-1]3-amino-2,4,6-triiodobenzoic acid</strong> is suspended in 220 ml. of water. After the dropwise addition of 24 ml. of a 30% aqueous sodium nitrite solution at 0 C., the pH value is brought down to 2 by adding dilute sulfuric acid. The batch is then stirred for one hour in an ice bath. By the gradual, dropwise addition of dilute sodium hydroxide solution, the batch is raised to pH 4.5, and the solution is allowed to stand under ice cooling. In the meantime, a solution of 20 g. of copper(I) chloride and 34 g. of potassium cyanide in 160 ml. of water has been prepared, warmed to 30 C., and the diazotization solution is added thereto all at once, under the occurrence of strong frothing. The mixture is stirred for another 15 minutes at 30 C. and then the copper salts are separated by acidifying the reaction solution to pH 3 with concentrated hydrochloric acid. The filtrate is brought to pH 0.5- 1 by the further addition of concentrated hydrochloric acid, and the precipitate, after several hours of agitation in an ice bath, is vacuum-filtered and washed with water. The compound, moist from vacuum-filtering, is suspended in 50 ml. of water, dissolved by adding dilute sodium hydroxide solution, and the solution is treated by stirring with activated carbon and filtered to a clear state. By adding drops of concentrated hydrochloric acid, the solution is brought to pH 0.5-1 and then stirred for several hours in an ice bath; the precipitate is vacuum-filtered. After washing with acetone-containing water and drying at 50 C., 16 g. (76% of theory) of 3-cyano-2,4,6-triiodobenzoic acid is obtained as a white powder, m.p. 238-240 C. (decomposition). |
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