2-(Chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride
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2-(Chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride
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CAS No:
86604-75-3
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Formula:
C9H12ClNO.ClH
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Chemical Name:
2-(Chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride
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Synonyms:
Pyridine,2-(chloromethyl)-4-methoxy-3,5-dimethyl-,hydrochloride (1:1);Pyridine,2-(chloromethyl)-4-methoxy-3,5-dimethyl-,hydrochloride;2-(Chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride;2-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine hydrochloride;CC-993;3,5-Dimethyl-2-chloromethyl-4-methoxypyridine hydrochloride;2-(Chloromethyl)-4-methoxy-3,5-dimethyl-1-pyridinium chloride;3,5-Dimethyl-4-methoxy-2-chloromethyl pyridine hydrochloride
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CAS No:
2-(Chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride Basic Attributes
222.11
221.037415
434-680-9
2933399090
Characteristics
22.1
3.24780
White to off White crystalline powder with irritating odour
127-128 °C
272.2°C at 760 mmHg
118.4ºC
Soluble in water.
Refrigerator, Under Inert Atmosphere
Safety Information
II
8
3261
3
34
26-36/37/39-45
P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, P501
H302
2-(Chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride Use and Manufacturing
To a solution [OF 4-METHOXY-3, 5-DIMETHYLPYRIDINEMETHANOL] (25.1 g, 0.15 mol) in dichloromethane (400 mL) was added a solution of thionyl chloride (18.8 g, 0. [158] mol) in dichloromethane (100 mL) over 30 min at room temperature under argon. After an additional 30 min of stirring at room temperature, the solvent was removed under reduced pressure. The solid residue was suspended in hexanes (200 mL) and filtered. The solid was washed with hexanes (50 mL) and air-dried to give 33.3 g (100percent) of the title compound as a white solid.To a solution of 4-methoxy-3, 5-dimethylpyridinemethanol (25.1 g, 0.15 mol) in dichloromethane (400 mL) was added a solution of thionyl chloride (18.8 g, 0.158 mol) in dichloromethane (100 mL) over 30 min at room temperature under argon. Ph3PO (43.78 g, 157.5 mmol) was dissolved in toluene (100 mL) in a 500 mL three-necked flask and BTC(14.84 g, 50 mmol) was dissolved in toluene (60 mL) and placed in a 150 mL constant pressure dropping funnel, BTC was added dropwise at room temperature, After the drop, the temperature is raised to 60 ° C.After incubation for 4 hours, 2-hydroxymethyl-4-methoxy-3, 5-dimethylpyridine (25.05 g, 150 mmol)Dissolved in toluene 75mL, at 40 ° C added to precipitate a white solid, incubation reaction 2 hours after stopping the reaction, The product was obtained by filtration to obtain a white solid which was dried to give 32.49 g of 2-chloromethyl-4-methoxy-3, 5-dimethylpyridine hydrochloride, the product yield was 98percentEXAMPLE 3 Hydrochloride acid (1.0 mL, 1.0 M in water) was added to 3, 5-dimethyl-4-(methoxy)-2-(chloromethyl)-pyridine (185.65 mg, 1.0 mmol) in ethanol (10 mL). The mixture was stirred for 1 h at room temperature and further filtered to give a clear solution. After the solution was kept in air for a week at room temperature, colorless crystals were obtained and indentified as 1. Yield: 92.6percent. IR (cm−1): 726.5 ν (C–Cl). 1H NMR (DMSO-d6) δ (ppm): 2.32 (s, 3H, m-CH3), 2.36 (s, 3H, m-CH3), 3.99 (s, 3H, p-OCH3), 5.09 (s, 2H, o-CH2-), 8.62(s, 1H, o-H). MS (FAB): m/z 186 [M+–Cl]. Anal. Calc. forC9H13NOCl2:C, 48.67; H, 5.90; N, 6.31. Found: C, 48.63;H, 5.88; N, 6.32percent.
Intermediate in the production of the antiulcer agent Omeprazole
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2-(Chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride
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