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CAS No. : | 50551-10-5 |
Formula : | C5H10N2O2 |
M.W : | 130.15 |
SMILES Code : | CCOC(=O)CC(N)=N |
MDL No. : | MFCD06797615 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-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 |
---|---|---|
47% | In ethyl acetate; for 0.333333h;Inert atmosphere; Reflux; | a. Preparation of ethyl 2-amino-lH-pyrrole-3-carboxylate. To a solution of carbethoxyacetamidine (390 mg, 3.0 mmol) in dried ethyl acetate (20 mL) under an argon atmosphere was rapidly added anhydrous chloroacetaldehyde under vigorous stirring at 22C. The reaction was stirred for 10 min and heated at reflux for 20 min. The mixture was cooled to room temperature and filtered through silica gel (15 g). The residue in the reaction flask was extracted with ethyl acetate (20 mL x 5), and filtered. The filtrate was collected and evaporated under reduced pressure to give 120 mg (47%) as a light yellow solid. [0090] 1H NMR: (500 MHz, CDC13) 5(ppm): 7.92 (br, 1H), 6.28 (t, J = 2.8 Hz, 1H), 6.15 (dd, J = 2.0 Hz, 1H), 4.94 (br, 2H), 4.24 (q, J = 7.1 Hz, 2H), 1.33 (t, J = 7.1 Hz, 3H). 13C NMR: (125 MHz, CDC13) 5(ppm): 166.5, 145.4, 110.3, 107.5, 94.5, 59.3, 14.7. |
39% | With triethylamine; In ethyl acetate; at 80℃; for 2h; | [00204] A solution of ethyl 3-amino-3-iminopropanoate (500 g, 3.0 mmol) and triethyl amine (0.5 mL, 3.60 mmol) in ethyl acetate (20 mL) was charged with anhydrous 2- chloroacetaldehyde (0.32 mL, 1.65 mmol) at room temperature. The resulting solution was heated to 80C for 2h. The reaction mixture was cooled to room temperature and filtered. The solid residue obtained was suspended in ethyl acetate (2 X 20 mL) and filtered. The combined filtrate was concentrated in vacuo to afford the title compound 1 as a viscous oil (100 mg, 39%). NMR (400 MHz, CDC13) delta 8.21 (br s, 1H), 6.25 (d, J=7.5 Hz, 1H), 6.18 (d, J=7.5 Hz, 1H), 5.04 (br s, 2H), 4.35 (q, J=7.1 Hz, 2H), 1.25 (t, J=7.1 Hz, 3H). |
31% | With ethyl acetate; In water; at 20 - 65℃; for 0.533333h; | Carbamimidoyl-acetic acid ethyl ester (3.357 g, 25.8 mmol) was dissolved in AcOEt (20 mL). Chloroacetaldehyde (50% solution in water, 1.8 mL, 28.7 mmol) was added rapidly at room temperature. The solution stirred for 2 minutes until a precipitant formed. The solution was then brought to 65 C. for 0.5 h. The reaction mixture was then cooled and flash chromatographed with AcOEt. Product containing fractions were concentrated to give the desired material as a green solid. 0.68 g obtained, 31% yield. 1H NMR (400 MHz, CDCl3) delta 1.32 (t, J=7.2 Hz, 3H), 4.24 (q, J=7.0 Hz, 2H), 5.08 (brs, 2H), 6.10-6.13 (m, 1H), 6.25 (t, J=3.12, 1 Hz), 8.60 (brs, 1H); MS Calcd.: 154. Found 155 (M+H). |
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; chloroform; at 50 - 60℃; | 15g (0.12mol, 1eq) of ethyl 3-amino-3-iminopropionate and 225 mL of tetrahydrofuran were added to the bottle, stirred and dissolved to obtain a solution of ethyl 3-amino-3-iminopropionate , placed in the beater system A.Add 114 g (0.75 mol, 6.5 eq) of 1,8-diazabicycloundec-7-ene (DBU) and 75 mL of THF to the beating bottle, stir well to obtain an alkaline solution, and place it in the beating system B in.The 200 g (0.13 mol, 1.1 eq) chloroacetaldehyde chloroform solution obtained in the previous step was added to a beating bottle and placed in the beating system C.Fill 180 mL white steel coils with THF, place the coils in a 60oC hot bath, and control the temperature between 50~60C.The respective beating speeds of the beating system A, the beating system B, and the beating system C are 2.30 g / min, 1.93 g / min, 2.14 g / min, and the three strands of materials converge at the tee.Then enter the coil for reaction with a retention time of 30 min.The receiving system concentrated the received product system containing 2-aminopyrrole-3-carboxylic acid ethyl ester to 40% at 40 C to obtain a viscous oily substance, namely 2-aminopyrrole-3-carboxylic acid ethyl ester. . The two-step yield was 48%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.4% | Adding 124 g of 1 mol of 2-chloroacetaldehyde dimethyl acetal (ie, the compound of formula III) to 500 ml of toluene to obtain an organic mixed solution of 2-chloroacetaldehyde dimethyl acetal; and then dichloroacetaldehyde dimethyl acetal Add 10 g of 0.05 mol of p-toluenesulfonic acid to the organic mixed solution, and warm to 50 C and stir for 2 h; then add 260 g of 2 mol of ethyl 3-amino-3-iminopropionate (ie, the compound of formula II) in 3 portions. The temperature was raised to 100 C for 2 h, filtered, and the filtrate was concentrated to give 150 g of 2-amino-3-carboxypyrrole ethyl ester, yield 97.4%.The next step reaction is carried out without purification |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.6% | 167 g, i.e., 1 mol of 2-bromomethyl-1,3-dioxolane (i.e., a compound of formula III) was added to 500 ml of 2-methyltetrahydrofuran to give 2-bromomethyl-1,3-dioxolane. The organic mixed solution is controlled to a temperature below 10 C; and then 100 ml of sulfuric acid (0.18 moL) with a mass fraction of 10% is added dropwise to the organic mixed solution of 2-bromomethyl-1,3-dioxolane. After stirring for 20 minutes, the liquid was separated, and 174 g of 1.33 mol of ethyl 3-amino-3-iminopropanoate (the compound of formula II) was added portionwise in the organic phase, and the mixture was heated to reflux at 100 C until the reaction was completed, and the filtrate was filtered. Concentration gave 144 g of 2-amino-3-carboxypyrroleethyl ester in a yield of 93.6%.The next step reaction is carried out without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | 152 g of 1 mol of 2-chloroacetaldehyde diethyl acetal (i.e., a compound of formula III) was added to 500 ml of toluene.Obtaining an organic mixed solution of 2-chloroacetaldehyde diethyl acetal, temperature control 10 C,Then add 100 ml to the organic mixed solution of 2-chloroacetaldehyde diethyl acetal.Concentrated hydrochloric acid (1.2 moL) with a substance concentration of 12 mol/L,Stir for 20 minutes after the addition is complete.Dissolve to obtain an organic phase,To the organic phase, 260 g of 2 mol of ethyl 3-amino-3-iminopropionate (ie, the compound of formula II) was added in three portions, and the mixture was heated to 80 C for 3 h, filtered, and the filtrate was concentrated to give 140 g of 2-amino- 3-carboxypyrroleethyl ester (i.e., a compound of formula IV) in a yield of 91%. |
Tags: 50551-10-5 synthesis path| 50551-10-5 SDS| 50551-10-5 COA| 50551-10-5 purity| 50551-10-5 application| 50551-10-5 NMR| 50551-10-5 COA| 50551-10-5 structure
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