Structure of 39799-77-4
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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. : | 39799-77-4 |
Formula : | C4H6N2O |
M.W : | 98.10 |
SMILES Code : | O=C1NC=CN1C |
MDL No. : | MFCD11520048 |
InChI Key : | PXHFWPOPKVWXQT-UHFFFAOYSA-N |
Pubchem ID : | 566589 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-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 |
---|---|---|
95% | EXAMPLE 4 Preparation of 1-methyl-4-imidazolin-2-one The procedure for the present Example was the same as that described in Example 3. N-(2,2-Diethoxyethyl)-N-methylurea (21.3 g, 0.11 mole) was dissolved in a mixture of methanol (520 ml) and water (260 ml) and a solution of 0.48 M HCl (310 ml) was stirred at room temperature for 2 days (TLC showed that the reaction was complete at 30 hours). The usual work-up described in the previous Example gave 1-methyl-4-imidazolin-2-one (10.5 g, 95%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; formaldehyd; In methanol; water; | EXAMPLE 19 Synthesis of 1-Methyl-3-hydroxymethyl-4-imidazolin-2-one A mixture of <strong>[39799-77-4]1-methyl-4-imidazolin-2-one</strong> (4 gms, 0.04 mol), 20 ml of formaldehyde (37% aqueous solution), sodium hydroxide (100 mg), and 20 ml of methanol was stirred at room temperature for 20 hours. After removing the solvent using a rotovap at reduced pressure, a liquid residue was obtained and filtered through a column of silica gel using chloroform as the eluent. The residue solidified after left standing overnight and was dissolved in water and then extracted with chloroform. The aqueous phase was concentrated and chromatographed through a column of silica gel G 60. Removal of the solvent afforded a solid which upon addition of acetone became white suspension. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In benzene; | EXAMPLE 7 Synthesis of 1-Methyl-4-imidazolin-2-one-3-methylenepivalate 1-Methyl-4-imidazolin-2-one (44 mg, 4.4*10-4 mol) and sodium hydride (20 mg) in dry benzene (20 ml) was stirred at room temperature for 2 hours. Chloromethylpivalate (71 mg) was added to the suspension and the reaction mixture was stirred for an additional 4 hours. After filtering the reaction mixture through filter paper, the filtrate was concentrated to give a liquid residue which was chromatographed through a column of silica gel to give a pure product (27 mg). T.l.c. Rf value was 0.77 using chloroform as the developing solvent system. 1 H n.m.r.(CDCl3): delta1.20(9H, s, C[CH3 ]3); 3.23(3H, s, CH3 -N); 5.55(2H, s, --NCH2 --O); 6.10 (1H, d, HC=CH); 6.38(1H, d, HC=CH). numax (film): 3190, 3150(NH); 1735, 1705(C=O); 1130 cm-1 (C-O-C). m/e 212, C10 H 16 N2)O3 requires 212. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | In water; benzene; | EXAMPLE 12 Synthesis of 1-Methyl-4-imidazolin-2-one-3-methylenedodecanoate 1-Methyl-4-imidazolin-2-one (300 mg, 0.003 mol) and sodium hydride (150 mg) were suspended in 10 ml of dry benzene in a dry flask. Chloromethyldodecanoate (0.77 gm, 0.003 mol) was added to the suspension. After the addition was complete, the reaction mixture was stirred at room temperature for 4 hours. The benzene was removed and the residue was taken up with chloroform (40 ml) followed by the addition of 20 ml of water. The chloroform layer was separated and the aqueous phase extracted with chloroform. The combined extracts were dried over anhydrous magnesium sulfate and concentrated to give a solid product. Column chromatography of the solid afforded I-methyl-4-imidazolin-2-one-3-methylenedodecanoate (400 mg, 43%), mp 41-42 C. T.l.c. Rf=0.24 using chloroform as the solvent system. HPLC Rt=5.57 min, acetonitrile(2):water(1), flow rate=2.0 ml/min. Found: C, 66.00; H, 9.40; N, 9.08. Calc for C17 H30 N2 O3: C, 65.77; H, 9.74; N, 9.02%. 1 H n.m.r.(CDCl3): delta0.88(3H, t, J=5 Hz, CH3 CH2 --); 1.35(18H, s, broad, CH3 [CH2 ]9 CH2 --); 2.30(2H, t, J=6 Hz, --COCH2 --); 3.2(3H, s, CH3 N--); 5.53(2H, s, --CH2 O--); 6.08(1H, d, J=3 Hz, HC=CH); 6.38(1H, d, J=3 Hz, HC=CH). numax (BKr): 3200, 3160, 3140(HC=CH); 1745, 1705(C=O); 1250 cm-1 (C-O-C) m/e 310, C17 H30 N2 O3 requires 310. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With hydrogenchloride; In methanol; water; | EXAMPLE 3 Preparation of 1-Methvl-4-imidazolin-2-one N-(2,2-Dimethoxyethyl)-N-methylurea (27.5 g, 0.17 mole) was dissolved in a mixture of methanol (670 ml) and water (340 ml). A solution of 0.48 M HCl (400 ml) was added dropwise from a dropping funnel. After stirring the reaction mixture for 3 days, it was neutralized with dilute NaOH solution. The pH of the solution was maintained neutral during the removal of the solvent by a rotovap under reduced pressure until a dry white solid remained in the flask. The solid was extracted four times with chloroform and the combined extracts were dried over anhydrous magnesium sulfate. Removal of the solvent gave 1-methyl-4 -imidazolin-2-one (15.5 g, 93%), mp 140-142 C. (sublimed). 1 H n.m.r. (CDCl3): delta3.27(3H, s, CH3 -N), 6.50(1H, t, J=2 Hz, HC=CH), 6.63(1H, t, J=2 Hz, HC=CH). (d6 -DMSO): delta3.11(3H, s, CH3 N); 6.30(1H, t, J=2 Hz, HC=CH); 6.38(1H, t, J=2 Hz, HC=CH); 11.67(1H, s, broad, NH, D2 O exchanged). numax (KBr): 1680(C=0; 1610, 1580 cm-1 (C=C). m/e 98, C4 H6 N2 O requires 98. HPLC Rt 3.10 min. TLC Rf value=0.08. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With Lawessons reagent; In toluene; for 18h;Inert atmosphere; Reflux; | In a dry 500 ml reaction flask,1-methyl-1,3-2H-imidazol-2-one was added under nitrogen and 110 g of Lawesson's reagent was added followed by 145 g of toluene followed by nitrogenGas protection under reflux reaction 18 hours; sample HPLC control to the reaction completely; the reaction is complete, vacuum distillationAfter distilling the toluene to one-third volume, cooling to room temperature, filtering to obtain a solid, washing the filter cake with an appropriate amount of tolueneAnd the resulting cake was put into 55 g of isopropyl alcohol while adding 1 g of activated charcoal to a temperature of 60 CAnd the filtrate is cooled to below 10 degrees. The filtrate is filtered and washed with cold isopropanol to obtain methimazole wet product. After vacuum drying, 21.4 g of methimazole is obtained. The yield is 72%. The obtained methimazole color is white crystal with 99.6% HPLC purity and less than 1000 ppb common metal ion content |