Water → 3-Pyridinecarboxylic acid, 2-[(phenylmethyl)thio]-

HRID 20249

反応式

HRID 20249 の反応式
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].[CH2:17]([SH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C)C=O>[C:18]1([CH2:17][S:24][C:8]2[C:9]([C:10]([OH:12])=[O:11])=[CH:13][CH:14]=[CH:15][N:16]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

6

反応物 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 762582-Chloronicotinic acid

生成物 1

HCID 7577793-Pyridinecarboxylic acid, 2-[(phenylmethyl)thio]-収率 71.49%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
140 °C

実験手順

In a stirred suspension of 96.37 g potassium carbonate in 700 gm dimethyl formamide, 100 gm 2-chloro nicotinic acid was charged. A solution of 82.38 g benzyl mercaptan in 300 gm dimethyl formamide was added in a period of two hours maintaining reaction temperature 80-90° C. The temperature of the reaction was raised up to 140° C. and then maintained for another three hours. 500 g water was added after completion of the reaction and solvent recovery. Product precipitation achieved by lowering the pH of the reaction mass by using dilute HCl. Product 2-(Phenyl methyl thio)-3-pyridine carboxylic acid precipitated completely till pH 4.5. After filtration and washing, cake was dried to get 110 g white to off white solid product 2-(Phenyl methyl thio)-3-pyridine carboxylic acid with 71.49% yield (Assay by HPLC 99.23%).

後処理

  1. additionwas charged
  2. temperaturemaintaining
  3. customreaction temperature 80-90° C
  4. temperaturemaintained for another three hours
  5. customafter completion of the reaction and solvent recovery
  6. customProduct precipitation
  7. customProduct 2-(Phenyl methyl thio)-3-pyridine carboxylic acid precipitated completely till pH 4.5
  8. filtrationAfter filtration
  9. washwashing
  10. customcake was dried

出典と根拠

ORDレコード
ord-f8d5243b73db43b5bb6aefa2d11b2d10
出典データセット
uspto-grants-2010_06
特許番号
US07745631B2

関連ノート

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