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Structure of Hydrazinylacetic acid
CAS No.: 14150-64-2
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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. : | 14150-64-2 |
Formula : | C2H6N2O2 |
M.W : | 90.08 |
SMILES Code : | O=C(O)CNN |
MDL No. : | MFCD11168310 |
InChI Key : | RRBZUCWNYQUCTR-UHFFFAOYSA-N |
Pubchem ID : | 84227 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H301-H311-H314-H331 |
Precautionary Statements: | P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P405-P501 |
Class: | 6.1(8) |
UN#: | 2928 |
Packing Group: | Ⅱ |
* 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 |
---|---|---|
96.9% | With hydrazine hydrate; In dichloromethane; at 5℃; | [0030] example 6 In a three- necked flask, 120 g (1.28 mol) of chloroacetic acid and 600 mL of dichloromethane were added, and the mixture was stirred at 5 C, and 96.4 g (1.54 mol) of hydrazine hydrate was slowly added thereto to carry out a reaction and dot plate monitoring for completion of the reaction. The reaction system was suction filtered, and the obtained solid was washed with a small portion of acetonitrile to give a white solid 111.7 g, yield: 96.9%, purity 99.5% |
With hydrazine; In water; for 24.0h; | Example 7:; preparation of LN- (11-METHYL LAURYL)-2N-CARBOXYMETHYL hydrazine; NH2-NH2 + CL-CH2COOH > NH2-NH-CH2COOH; Put 187.5 g (3.0 mol) of 80% hydrazine hydrate into a 1000-ml flask containing a solution of 94.5 g (1.0 mol) of chloroacetic acid in 100 ml of water. Setting for 24 hours, acidifying to pH = 6, cooling and filtrating the crystallization, 61.2 g (0.68 mol) of hydrazine acetic acid was produced. Those hydrazine acetic acid was added into a mixture of 74.3 g (0.34 mol) of 11-METHYL lauryl chloride, 28.6 g (0.34 mol) of sodium bicarbonate, and 340 ml of 95% alcohol, stirring and refluxing for 10 hours. Finally, after decoloring with activated charcoal, acidifying to pH=6, cooling, filtrating and crystallizing, 68. Og of 1N- (11-methyl lauryl) -2N-carboxymethyl hydrazine was obtained. A total yield: 25.0%. (C: 66. 03% ; H: 11.64% ; N: 10.52% ; O : 11.73%.) MS: 272.43, 254.41, 169.33, 127.25, 43.08. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.25 g (100%) | EXAMPLE 7 α-Hydrazinoacetic acid The Boc-α-hydrazinoacetic acid (1.90 g, 0.01 mol) was dissolved in 4N HCl in ethyl acetate (20 ml). The precipitate that formed was isolated by decantation and was triturated with ethyl ether. Yield, 1.25 g (100%); Rf =0.1 (nBuOH-H2 O-HOAc, 4:1:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; In ethanol; for 10.0h;Heating / reflux; | Example 7:; preparation of LN- (11-METHYL LAURYL)-2N-CARBOXYMETHYL hydrazine; NH2-NH2 + CL-CH2COOH > NH2-NH-CH2COOH; Put 187.5 g (3.0 mol) of 80% hydrazine hydrate into a 1000-ml flask containing a solution of 94.5 g (1.0 mol) of chloroacetic acid in 100 ml of water. Setting for 24 hours, acidifying to pH = 6, cooling and filtrating the crystallization, 61.2 g (0.68 mol) of hydrazine acetic acid was produced. Those hydrazine acetic acid was added into a mixture of 74.3 g (0.34 mol) of 11-METHYL lauryl chloride, 28.6 g (0.34 mol) of sodium bicarbonate, and 340 ml of 95% alcohol, stirring and refluxing for 10 hours. Finally, after decoloring with activated charcoal, acidifying to pH=6, cooling, filtrating and crystallizing, 68. Og of 1N- (11-methyl lauryl) -2N-carboxymethyl hydrazine was obtained. A total yield: 25.0%. (C: 66. 03% ; H: 11.64% ; N: 10.52% ; O : 11.73%.) MS: 272.43, 254.41, 169.33, 127.25, 43.08. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
292.6 g | 184.8 g of the above obtained solid was dissolved in 920 mL of ethanol solution, stirred at -20 C, and 184.8 mL of thionyl chloride was slowly added dropwise, and stirred for 10 min. The oil bath was heated to reflux reaction, and the reaction completion is monitored by dot plate . The excess solvent was evaporated under reduced pressure to give Ethyl hydrazinoacetate 231.7 g (yield: 97.3%). The above-mentioned Ethyl hydrazinoacetate was placed in a 2000 mL three-necked flask, and 1000 mL of an anhydrous ethanol solution having a hydrogen chloride concentration of not less than 12 mol/L was added at room temperature, stirred for 30 minutes, and heated to reflux reaction, and the reaction completion is monitored by dot plate . The reaction system was cooled, and the precipitated solid was dried to give ethyl hydrazinoacetate hydrochloride as a white solid, which was purified from ethanol to afford 292.6 g of white crystals, the yield was 96.9% and the purity was 99.7% |