Potassium Carbonate → 2-Chloromethyl-3-methyl-4-(2-morpholinoethylthio)pyridine

HRID 1720051ノート

反応式

HRID 1720051 の反応式
O[CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([S:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:21])=O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[Cl:21][CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([S:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:6]=[CH:5][N:4]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 199630392-Hydroxymethyl-3-methyl-4-(2-morpholinoethylthio)pyridine

生成物 1

HCID 199630342-Chloromethyl-3-methyl-4-(2-morpholinoethylthio)pyridine

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

2-Hydroxymethyl-3-methyl-4-(2-morpholinoethylthio)pyridine (6.2 g) was dissolved in chloroform and thereto was dropwise added thionyl chloride (2 ml) under ice-cooling. The mixture was stirred at room temperature for 1 hour. After the completion of the reaction, the reaction mixture was poured into ice-water and made alkaline with potassium carbonate, followed by extraction with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and the solvent was distilled away to give 6.0 g of 2-chloromethyl-3-methyl-4-(2-morpholinoethylthio)pyridine as an oily substance. The substance was added to ethanol (60 ml) containing a solution of 5-methoxycarbonyl-2-mercaptobenzimidazole (5.1 g) and sodium hydroxide (1.6 g) in water (10 ml) and the mixture was refluxed under heating for 3.5 hours. After the completion of the reaction, the ethanol was distilled away and the residue was dissolved in water. The aqueous layer was washed with chloroform and dilute hydrochloric acid was dropwise added until crystals precipitated in the aqueous layer. The resultant crystals were collected by filtration to give 2-((3-methyl-4-(2-morpholinoethylthio)-2-pyridyl)methylthio)-1H-benzimidazole-5-carboxylic acid 7/2 hydrate, melting point 120°-124° C.

後処理

  1. temperaturecooling
  2. customAfter the completion of the reaction
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away

出典と根拠

ORDレコード
ord-fa9f500d2ec04b07813f714f163002ec
出典データセット
uspto-grants-1996_04
特許番号
US05504082

反応ノート

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