Methyl iodide → HCID 20098207、化合物

HRID 1768919

反応式

HRID 1768919 の反応式
Br[C:2]1[N:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([CH3:20])[CH3:19])=[CH:13][CH:12]=2)[C:3]=1[C:4]([OH:6])=[O:5].N[C:22](N)=S.[OH-].[Na+].SC1N=CC=C(C2C=CC(OC(C)C)=CC=2)C=1C(O)=O.[CH3:47][C:48]1[CH:53]=[C:52]([CH3:54])[N:51]=[C:50]([S:55](C)(=O)=O)[N:49]=1.C(=O)([O-])[O-].[K+].[K+].CI>Cl.C(O)(=O)C.CS(C)=O.O>[CH:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([C:7]2[C:3]([C:4]([O:6][CH3:22])=[O:5])=[C:2]([S:55][C:50]3[N:51]=[C:52]([CH3:54])[CH:53]=[C:48]([CH3:47])[N:49]=3)[N:10]=[CH:9][CH:8]=2)=[CH:12][CH:13]=1)([CH3:20])[CH3:19]

参加物

12

反応物 7

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 27723824,6-Dimethyl-2-methylsulfonylpyrimidineHCID 20095254HCID 20095254、化合物HCID 178458232HCID 178458232、化合物

生成物 1

HCID 20098207HCID 20098207、化合物収率 26.9%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 313Hydrochloric Acid溶媒2 回HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒2 回

実験手順

20.0 g (0.059 mol) of 2-bromo-4-(4-isopropoxyphenyl)nicotinic acid and 5.5 g (0.072 mol) of thiourea were dissolved in 40 ml of 5% HCl and 60 ml of acetic acid, and stirred at 100° C. for 2 hours. The reaction mixture was poured into water, and 200 ml of 50% sodium hydroxide was added thereto, and the mixture was stirred at room temperature for 30 minutes. The mixture was then acidified with 20% HCl and the thus precipitated was filtrated out and washed with water and then dried. The above synthesized crude crystal [2-mercapto-4-(4-isopropoxyphenyl)nicotinic acid] and 11.1 g (0.060 mol) of 4,6-dimethyl-2-methylsulfonylpyrimidine, and 25.0 g (0.18 mol) of potassium carbonate were dissolved in 200 ml of dimethylsulfoxide and stirred at 80° C. for 2 hours. After restoring the temperature to room temperature, 16.8 g (0.12 mol) of methyl iodide was added to the reaction mixture, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was then poured into water, and was extracted with 500 ml of ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and concentrated. The concentrate was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=1/2) to obtain 6.5 g of a light-yellowish thick syrup-like aimed product.

後処理

  1. additionwas added
  2. customthe thus precipitated
  3. filtrationwas filtrated out
  4. washwashed with water
  5. customdried
  6. stirringstirred at 80° C. for 2 hours
  7. customto room temperature
  8. stirringthe mixture was stirred at room temperature for 30 minutes
  9. extractionwas extracted with 500 ml of ethyl acetate
  10. washThe organic layer was washed with water
  11. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  12. concentrationconcentrated
  13. customThe concentrate was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=1/2)

出典と根拠

ORDレコード
ord-3c8f7742f3c943b9aba6ba9f032dadfc
出典データセット
uspto-grants-1995_01
特許番号
US05380700

関連ノート

読み込み中…