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CAS No. : | 1943-83-5 | MDL No. : | MFCD00002043 |
Formula : | C3H4ClNO | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | BCMYXYHEMGPZJN-UHFFFAOYSA-N |
M.W : | 105.52 | Pubchem ID : | 16035 |
Synonyms : |
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Signal Word: | Danger | Class: | 6.1,3 |
Precautionary Statements: | P264-P210-P240-P241-P242-P243-P285-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P331-P310-P330-P370+P378-P363-P403+P233-P405-P501 | UN#: | 3080 |
Hazard Statements: | H226-H314-H334-H301+H311+H331 | Packing Group: | Ⅱ |
GHS Pictogram: |
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* 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 |
---|---|---|
EXAMPLE 1; EPO <DP n="33"/>This example illustrates one protocol for the preparation of ((2,3- dimethylphenyl)methyl)-l,3-oxazolin-2-ylamine (Compound A25) A mixture of 1.0 gram (0.0074 mole) of <strong>[51586-20-0]2,3-dimethylbenzylamine</strong> and 0.69 gram (0.0081 mole) of 2-chloroethylisocyanate in 10 mL of 1,4-dioxane was heated to reflux where it stirred for about 18 hours. The reaction mixture was allowed to cool and an aqueous solution of sodium hydroxide (4.0 mL of a 3.0 molar solution) was added. The reaction mixture was heated to reflux for about 18 hours then allowed to cool to ambient temperature. The reaction mixture was concentrated under reduced pressure to leave a viscous oil residue. The residue was suspended in 50 mL of ethyl acetate and washed with 20 mL of water. The organic phase was extracted with 20 mL of 3.0 molar aqueous hydrochloric acid. The aqueous extract was made basic by adding 3.0 molar aqueous sodium hydroxide and the basic mixture was extracted with 50 mL of ethyl acetate. The extract was dried with sodium sulfate, filtered and the filtrate concentrated under reduced pressure to yield 0.81 gram of the title compound as an oil. The NMR spectrum was consistent with the proposed structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With triethylamine; In tetrahydrofuran; at 20℃; for 45h;Heating / reflux; | EXAMPLE 35; Synthesis of l-(5-acetyl-4-methylthiazol-2-yl)imidazolidin-2-one; To a solution of <strong>[30748-47-1]5-acetyl-2-amino-4-methylthiazole</strong> (5.50 g, 35.20 mrnol) in tetrahydrofuran (200 mL) was added triethylamine ( 1 5.0 mL, 107.6 mrnol) and 2- chloroethyl isocyanate (3.90 mL, 45.70 mrnol). The reaction mixture was stirred at ambient temperature for 18 hours, and then heated to reflux for 27 hours. The solvent was removed in vacuo, and the residue was washed with water (200 mL) and ethyl acetate/hexanes ( 1 /1 , 50 mL) to afford the title compound in 99% yield (7.9 g): MS (ES+) m/z 226.1 (M + 1 ). |
99% | With triethylamine; In tetrahydrofuran; at 20℃; for 45h;Reflux; | To a solution of <strong>[30748-47-1]5-acetyl-2-amino-4-methylthiazole</strong> (5.50 g, 35.20 mmol) in tetrahydrofuran (200 mL) was added triethylamine (15.0 mL, 107.6 mmol) and 2-chloroethyl isocyanate (3.90 mL, 45.70 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, and then heated to reflux for 27 hours. The solvent was removed in vacuo, and the residue was washed with water (200 mL) and ethyl acetate/hexanes (1/1, 50 mL) to afford the title compound in 99% yield (7.9 g): MS (ES+) m/z 226.1 (M + 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | EXAMPLE 3; Synthesis of ethyl 4-methyl-2-(2-oxoimidazolidin-l-yl)thiazole-5-carboxylate; To a solution of ethyl 2-aιnino-4-ιnethylthiazole-5-carboxylate (9.31 g, 49.99 minol) in tetrahydrofuran (200 rnL) was added 2-chloroethyl isocyanate (5.50 rnL, 64.0 minol) at ambient temperature. The resulting reaction mixture was heated to reflux for 7 hours, followed by the addition of potassium carbonate (8.30 g, 60.0 mmol) and tetra-ϖ- butylammonium iodide (0.50 g, 1.35 mmol) and the resulting mixture was heated to reflux for 23 hours. The solvent was removed in vacuo, and the residue was washed with water (200 mL) and ethyl acetate (50 mL) to afford the title compound in 71% yield (9.10 g): mp 197-199 0C; 1H NMR (300 MHz, DMSCW6) δ 7.83 (s, I H), 4.20-3.93 (m, 4H), 3.49-3.43 (m, 2H), 2.46 (s, 3H), 1.20 (t, J = 6.9 Hz, 3H); MS (ES+) m/z 256.3 (M + 1 ). | |
71% | To a solution of ethyl 2-amino-4-methylthiazole-5-carboxylate (9.31 g, 49.99 mmol) in tetrahydrofuran (200 ml_) was added 2-chloroethyl isocyanate (5.50 ml_, 64.0 mmol) at ambient temperature. The resulting reaction mixture was heated to reflux for 7 hours, followed by the addition of potassium carbonate (8.30 g, 60.0 mmol) and tetra-n-butylammonium iodide (0.50 g, 1.35 mmol) and the resulting mixture was heated to reflux for 23 hours. The solvent was removed in vacuo, and the residue was washed with water (200 ml_) and ethyl acetate (50 ml_) to afford the title compound in 71% yield (9.10 g): mp 197-199 C; 1H NMR (300 MHz, DMSO-d6) 8 7.83 (s, 1H), 4.20-3.93 (m, 4H), 3.49-3.43 (m, 2H), 2.46 (s, 3H), 1.20 (t, J = 6.9 Hz, 3H); MS (ES+) m/z 256.3 (M + 1)- |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | (R)-alphamethyl-4-nitrobenzylamine hydrochloride (645 mg, 0.32 mmole) was suspended in 5 ml tetrahydrofuran and stirred with triethylamine (330 mg) for 1 hour. 2-chloroethylisocyanate (360 mg, 95%) was added in 5 ml tetrahydrofuran with stirring and the mixture stirred for 4 hours. 6 ml of water was then added followed by 2 ml 10 molar sodium hydroxide and the mixture heated to reflux for 24 hours. The mixture was then diluted with 50 ml ethyl acetate and shaken. The aqueous phase was discarded and the organic layer washed with 5 ml water, then extracted twice with 5 ml 1 molar hydrochloric acid. The extracts were combined and basified with 10 molar sodium hydroxide. The precipitated product was extracted with 25 ml ethyl acetate, washed with water and then reduced to dryness in vacuo. The product forms pale yellow crystals on drying, mp. 112-116 C. Yield 0.62 g (83%). Proton nmr in CDCl3 shows 7.8 (4H dd, J=9 and 42 Hz), 4.8 (1Hq, J=7 Hz), 3.9 (4Hm) 1.4(3H d, J=7 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at 20℃; for 15h; | Step 1 3,2 g (20.6mmol) 1-(2-chlorophenyl)ethaneamine [CAS 39959-67-6] and 52.3 g (22.6 mmol) triethylamine were given into 20 ml dichloromethane and afterwards 2.4 g (22.6 mmol) 2-chloroethylisocyanat werde added dropwise. The mixture was allowed to react 15 hours at 20C. The volatile components were evaporated to give 1-(2-chloroethyl)-3-[1-(2-chlorophenyl)ethyl]urea (log p = 2.3) that was used in step 2 without further purification |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | In tetrahydrofuran; at 0 - 20℃; | Example 13 A 0 C. suspension of <strong>[25850-22-0]2,2-dimethyltetrahydro-2H-pyran-4-amine</strong> (0.806 g, 6.24 mmol) in THF (30 mL) was treated drop-wise with 2-chloroethyl isocyanate (0.585 mL, 6.86 mmol), allowed to warm to RT as the cooling bath expired and stirred overnight. The mixture was treated with additional 2-chloroethyl isocyanate (160 muL) and stirred at RT for an additional 24 hours, then concentrated to dryness, the residue dissolved in EtOAc and washed with saturated NH4Cl (1*), NaHCO3 (1*) and brine (1*), dried over MgSO4 and concentrated to dryness to afford 1-(2-chloroethyl)-3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)urea (700 mg, 48%) as a yellow oil. MS (ESI) m/z: 235.1 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71.33% | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 15h;Reflux; | 3-(3-benzyloxy)pyrazin-2-amine (100 mg, 0.50 mmol) and 2-chloroethyl isocyanate (50 muL, 0.60 mmol), DIPEA (0.26 mL, 1.50 mmol) was dissolved in tetrahydrofuran (0.25 M ) and heated under reflux for 15 hours. After completion of the reaction, the solvent was concentrated under reduced pressure, and the residue was purified by column chromatography (ethyl acetate / n-hexane = 1/2) to give the title compound 109 mg at a yield of 71.33%. |
71.3% | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 18h;Inert atmosphere; Schlenk technique; Reflux; | General procedure: 2-Chloroethyl isocyanate (0.1 mL, 1.1 mmol) was added to a solutionof the appropriate 2-amino-3-benzyloxy pyrazine derivative(0.92 mmol) in dry THF (5 mL) in the presence of DIPEA (0.5 mL,2.75 mmol). The reaction mixture was refluxed for 18 h and evaporatedafter cooling. The residue was purified by flash columnchromatography (SiO2, EA/n-Hex 1/4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; for 1h;Cooling with ice; | Step A: tert-butyl 6-(3 -(2-chloroethyl)ureido)-3-azabicyclo [3.1 . Olhexane-3 -carboxylate: To anice-cooled DCM (10 ml) solution of <strong>[208837-83-6]tert-butyl 6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate</strong> (1.01 g, 5.09 mmol) was added triethylamine (1.775 mL, 12.74 mmol) and then 2-chloroethyl isocyanate (0.59 1 g, 5.60 mmol). After 1 hour, the reaction mixture was quenched with aqueous sodium bicarbonate and the aqueous layer was extracted with DCM (3 X 10 mL). The combined organic layers were then dried over sodium sulfate, filtered and concentrated in vacuo to afford tert-butyl 6-(3-(2-chloroethyl)ureido)-3-azabicyclo[3.1 .0]hexane-3-carboxylate which was used without further purification. |