Sulfuric Acid → Methyl 3-hydroxy-4-phenylthiobenzoate

HRID 37145

反応式

HRID 37145 の反応式
N[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5](O)=[S:6].S(=O)(=O)(O)O.N[C:23](N)=[O:24].N(O)=[O:27].S([O-])([O-])(=O)=O.[Na+].[Na+]>O>[OH:27][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([O:24][CH3:23])=[S:6]

参加物

7

反応物 5

HCID 1118Sulfuric Acid2 回HCID 1176UreaHCID 24436Sodium SulfateHCID 24529Nitrous AcidHCID 1785077933-Amino-4-phenylthiobenzoic acid

生成物 1

HCID 54152449Methyl 3-hydroxy-4-phenylthiobenzoate

試薬・触媒・溶媒 1

HCID 962Water溶媒3 回

反応条件

温度
-5 °C

実験手順

Adding 110.27 g of 3-amino-4-phenylthiobenzoic acid to 400 ml heated water solution of concentrated sulfuric acid (81 ml), the mixture was heated and stirred for 2 hours, and cooled with ice-salt bath to -5° C. To this solution, a 80 ml water solution of 36.25 g of sodium nitride which was ice-cooled was added in about 1 hour. Further stirring for 30 minutes at 0 ° to 5° C., 2 g of urea was added and stirred for 30 minutes, and the unreacted nitrous acid was decomposed, the obtained mixture was gradually added to a mixture of 121 ml of concentrated sulfuric acid, 168 g of anhydrous sodium sulfate and 112 ml of water, while stirring, in 75 minutes at 100° to 110° C. After addition, the mixture was further stirred for 1 hour at the same temperature. The reaction mixture was cooled, and precipitating brown granules were filtered, washed with water, and dried overnight at 50° C. The obtained product was added to the mixture of 1.4 liters of methanol and 70 ml of concentrated sulfuric acid, and the mixture was refluxed for 2 hours while stirring. After termination of reaction, the reaction mixture was concentrated in vacuo, and 1.5 liters of water was added to the residue, and the product was extracted with ethyl acetate (500 ml×3). The extract was dried in anhydrous sodium sulfate, and concentrated in vacuo. The residue was extracted in 4.2 liters of hot hexane, and cooled, and precipitating yellow matter was filtered, and 49.37 g of methyl 3-hydroxy-4-phenylthiobenzoate was obtained.

後処理

  1. temperaturethe mixture was heated
  2. temperaturecooled
  3. additionwas added in about 1 hour
  4. stirringFurther stirring for 30 minutes at 0 ° to 5° C.
  5. stirringstirred for 30 minutes
  6. stirringwhile stirring, in 75 minutes at 100° to 110° C
  7. additionAfter addition
  8. stirringthe mixture was further stirred for 1 hour at the same temperature
  9. temperatureThe reaction mixture was cooled
  10. customprecipitating brown granules
  11. filtrationwere filtered
  12. washwashed with water
  13. customdried overnight at 50° C
  14. additionThe obtained product was added to the mixture of 1.4 liters of methanol and 70 ml of concentrated sulfuric acid
  15. temperaturethe mixture was refluxed for 2 hours
  16. stirringwhile stirring
  17. customAfter termination of reaction
  18. concentrationthe reaction mixture was concentrated in vacuo, and 1.5 liters of water
  19. additionwas added to the residue
  20. extractionthe product was extracted with ethyl acetate (500 ml×3)
  21. dry with materialThe extract was dried in anhydrous sodium sulfate
  22. concentrationconcentrated in vacuo
  23. extractionThe residue was extracted in 4.2 liters of hot hexane
  24. temperaturecooled
  25. customprecipitating yellow matter
  26. filtrationwas filtered

出典と根拠

ORDレコード
ord-c1f28bfeb68d4a92b2ab44e6fd264e34
出典データセット
uspto-grants-1995_05
特許番号
US05420128

関連ノート

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