Structure of 55329-22-1
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CAS No. : | 55329-22-1 |
Formula : | C6H7ClN2O2S |
M.W : | 206.65 |
SMILES Code : | CC1=NC(=NC(Cl)=C1)S(C)(=O)=O |
MDL No. : | MFCD11109839 |
InChI Key : | OLOLDTJCNAOMQJ-UHFFFAOYSA-N |
Pubchem ID : | 12397672 |
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 |
---|---|---|
(2) Synthesis of the Compound No. II-4 from the intermediate In THF, an alkoxide was prepared from benzyl alcohol (1.65 g, 0.010*1.5 mol) and NaH (0.43 g, (ca. 60% in mineral oil), 0.010*1.05 mol). The Compound No. VIII-4 (2.10 g, 0.010 mol) obtained from the preceding section (1) was added thereto and allowed to react for 2 hours at room temperature. The reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate to separate an organic phase. The organic phase was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated, and thereafter the residue was purified on a silica gel column to obtain the title compound as an oily product. Yield: 1.31 g (56%). 1 H-NMR (60 MHz, CDCl3, delta): 2.37(3H,s), 5.33(2H,s), 6.73(1H,s), 7.1-7.6(5H,m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 3-chloro-benzenecarboperoxoic acid; In chloroform; | Reference Synthesis Example 3 Synthesis of 4-chloro-6-methyl-2-(methylsulfonyl)pyrimidine (Compound III-7) 4-Chloro-6-methyl-2-(methylthio)pyrimidine (Compound IV-7) (2.0 g, 0.0114 mol) was dissolved in chloroform, m-chloroperbenzoic acid (5.64 g, (purity ca. 70%), 0.0114*2.0 mol) was added thereto and the solution was stirred for about 2 hours at room temperature. The reaction solution was partitioned between chloroform and saturated aqueous sodium hydrogen carbonate to separate an organic phase, which was then washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, concentrated, and thereafter, purified on silica gel column to obtain the compound (III-7). Yield: 2.25 g (95%). m.p. 67 to 70 C. 1 H-NMR (60 MHz, CDCl3, delta): 2.63(3H,s), 3.30(3H,s), 7.38 (1H,s). | |
With 3-chloro-benzenecarboperoxoic acid; In chloroform; | (1) Synthesis of an intermediate, 4-chloro-6-methyl-2-(methylsulfonyl)pyrimidine (Compound No. VIII-4) 4-Chloro-6-methyl-2-(methylthio)pyrimidine (2.0 g, 0.0114 mol) (Compound No. VII-4) was dissolved in chloroform, and m-CPBA (5.64 g (purity ca.70%), 0.0114*2.0 mol) was added thereto, and then the resulting solution was allowed to react for about 2 hours at room temperature. The reaction solution was partitioned between chloroform and aqueous saturated sodium hydrogen carbonate to separate an organic phase. The organic phase was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated, thereafter the residue was purified on a silica gel column to obtain the Compound No. VIII-4. | |
With sodium hypochlorite; chlorine; In hydrogenchloride; water; | EXAMPLE 10 STR124 1.9 l of sodium hypochlorite (about 150 g of active chlorine per liter) were added slowly to a solution of 175 g (1 mole) of 2-methylmercapto-4-methyl-6-chloropyrimidine in 375 ml of concentrated hydrochloric acid and 375 ml of water at 5 C. The product which had precipitated was then filtered off and rinsed with water. This gave 170 g (82% of theory) of 2-methylsulfonyl-4-methyl-6-chloropyrimidine in the formn of colorless crystals of melting point 72 C. STR125 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dimethyl sulfoxide; | The above synthesis may be carried out as follows: To N-cyanoethylglycine, ethyl ester (15.9 g, 102 mmol) (a compound of formula (Y2)) dissolved in DMSO (70 mL) was added <strong>[55329-22-1]4-chloro-6-methyl-2-methylsulfonylpyrimidine</strong> (18.8 g, 91 mmol) (a compound of formula (Y1)) and diisopropylethylamine (18 mL, 100 mmol). After stirring for 16 hours, the reaction temperature was raised to 70 C. and imidazole (26.5 g, 0.39 mol) was added. After stirring for 1 day, the reaction was cooled to ambient temperature and added to ice water. The solid that formed was suction filtered and collected on paper to give 9.9 g of 2-[(2-cyanoethyl)[2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]acetic acid, ethyl ester (a compound of formula (Yc1)). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzyl alcohol; In tetrahydrofuran; mineral oil; | Synthesis Example 3 Synthesis of 4-chloro-6-methyl-2-(phenylmethoxy)pyrimidine (Compound I-240) In tetrahydrofuran, benzyl alcohol (Compound II-64) (1.65 g, 0.010*1.5 mol) and sodium hydride (ca. 0.43 g, (60% in mineral oil), 0.010*1.05 mol) were mixed to form an alkoxide. 4-Chloro-6-methyl-2-(methylsulfonyl)pyrimidine (Compound III-7) (2.10 g, 0.010 mol) was added thereto and was allowed to react for 2 hours at room temperature. The reaction solution was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate, the organic phase was separated and washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated, and thereafter, purified on silica gel column to obtain the compound (I-240) as an oily product. Yield: 1.31 g (56%). 1 H-NMR (60 MHz, CDCl3, delta): 2.37(3H,s), 5.33(2H,s), 6.73(1H,s), 7.1-7.6(5H,m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | In tetrahydrofuran; | EXAMPLE 2 Preparation of 4-chloro-2-(N-formylanilino)-6-methylpyrimidine (Compound 6) Formanilide (2.3 g) was added to a suspension in 50 ml of tetrahydrofuran of 0.9 g of sodium hydride (60%) of which oily component was removed with n-hexane, and the mixture was stirred at room temperature for 2 hours. To this was added 3.5 g of <strong>[55329-22-1]4-chloro-6-methyl-2-methylsulfonylpyrimidine</strong> and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2.0 g (yield: 48%) of 4-chloro-2-(N-formylanilino)-6-methylpyrimidine having a melting point of 150-152 C. |
48% | In tetrahydrofuran; | EXAMPLE 2 Preparation of 4-chloro-2-(N-formylanilino)-6-methylpyrimidine (Compound 6) Formanilide (2.3 g) was added to a suspension in 50 ml of tetrahydrofuran of 0.9 g of sodium hydride (60%) of which oily component was removed with n-hexane, and the mixture was stirred at room temperature for 2 hrs. To this was added 3.5 g of <strong>[55329-22-1]4-chloro-6-methyl-2-methylsulfonylpyrimidine</strong> and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2.0 g (yield: 48%) of 4-chloro-2-(N-formylanilino)-6-methylpyrimidine having a melting point of 150 - 152 C. |
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