Method for preparing 4-methyl-2-sulfomethyl-1(3)H-imidazole
A technology of thiomethyl and methylisothiourea, which is applied in the field of synthesis of 4-methyl-2-thiomethyl-1H-imidazole, can solve the problems of difficult control of the reaction, inconvenient operation, and low synthesis yield. Achieve the effects of easy amplification, increased yield, and shortened synthetic routes
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Embodiment 1
[0009] Example 1: Dissolve 150 mg (1.62 mmol) of chloroacetone in 5 mL of N,N-dimethylformamide (DMF), and then add 1.62 mmol of S-methylisothiourea (or its phase corresponding to the various salts), 448 mg (3.24 mmol) of K 2 CO 3 , 24 mg (0.16 mmol) of NaI, heated to 80°C, and stirred overnight (12-16 hours). Then the reaction solution was cooled, poured into ice water, extracted with ethyl acetate (100 ml*4), the organic phase was washed twice with saturated brine, the organic phase was combined, and anhydrous Na 2 SO 4 After drying and filtering, the filtrate was concentrated under reduced pressure to obtain 160 mg of crude 4-methyl-2-thiomethyl-1(3)H-imidazole, which was purified by column chromatography to obtain 148 mg of the product, yield: 71.2%.
Embodiment 2
[0010] Embodiment 2: 15 g (162 mmol) of chloroacetone are dissolved in 500 mL of DMF, and then 162 mmol of S-methylisothiourea (or its corresponding various salts) are added successively, 44.8 g (324 mmol ) of K 2 CO 3 , 2.4 g (16 mmol) of NaI, heated to 80°C, and stirred overnight. Then the reaction solution was cooled, poured into ice water, extracted with ethyl acetate (1000 ml*4), the organic phase was washed twice with saturated brine, the organic phase was combined, and anhydrous Na 2 SO 4 After drying and filtering, the filtrate was concentrated under reduced pressure to obtain 16.5 g of crude 4-methyl-2-thiomethyl-1(3)H-imidazole, which was purified by column chromatography to obtain 15 g of the product, yield: 72.1%.
Embodiment 3
[0011] Embodiment 3: the chloracetone of 150 g (1.62mol) is dissolved in the DMF of 5000 mL, then add the S-methylisothiourea (or its corresponding various salts) of 1.62 mol successively, 448 g (3.24 mol) of K 2 CO 3 , 24 g (0.16 mol) of NaI, heated to 80°C, and stirred overnight. Then the reaction solution was cooled, poured into ice water, extracted with ethyl acetate (10L*4), the organic phase was washed twice with saturated brine, the organic phase was combined, and anhydrous Na 2 SO 4 After drying and filtering, the filtrate was concentrated under reduced pressure to obtain 168 g of crude 4-methyl-2-thiomethyl-1(3)H-imidazole, which was purified by column chromatography to obtain 151 g of the product, yield: 72.5%.
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