Water → 4-(4-Chlorophenyl)-2-(4,6-dimethoxypyrimidin-2-ylthio)nicotinic acid

HRID 1768917ノート

反応式

HRID 1768917 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16]C)=[O:15])=[C:12]([S:18][C:19]3[N:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[N:20]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([OH:16])=[O:15])=[C:12]([S:18][C:19]3[N:20]=[C:21]([O:27][CH3:28])[CH:22]=[C:23]([O:25][CH3:26])[N:24]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 20095260Methyl 4-(4-chlorophenyl)-2-(4,6-dimethoxypyrimidin-2-ylthio)nicotinate

生成物 1

HCID 157671394-(4-Chlorophenyl)-2-(4,6-dimethoxypyrimidin-2-ylthio)nicotinic acid収率 70.8%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
60 °C

実験手順

16.8 g (0,040 mol) of methyl 4-(4-chlorophenyl)-2-(4,6-dimethoxypyrimidin-2-ylthio)nicotinate was dissolved in 150 ml of dimethylsulfoxide, and 35 ml (0,070 mol) of 2N sodium hydroxide added with stirring at 60° C. After stirring at 60° C. for 30 minutes, the mixture was poured into water, and washed twice with ethyl acetate. The aqueous layer was acidified with 10% hydrochloric acid, and extracted with 500 ml of ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and concentrated. The concentrate was washed with methanol and isopropyl ether to obtain 11.5 g of a white crystal of the aimed product.

後処理

  1. stirringAfter stirring at 60° C. for 30 minutes
  2. washwashed twice with ethyl acetate
  3. extractionextracted with 500 ml of ethyl acetate
  4. washThe extract was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. washThe concentrate was washed with methanol and isopropyl ether

出典と根拠

ORDレコード
ord-5271d012d89d4083b6cdf1a7e0935afe
出典データセット
uspto-grants-1995_01
特許番号
US05380700

反応ノート

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