Sulfuric Acid → Ethanol, 2-((4-amino-3-methylphenyl)ethylamino)-, sulfate (1:1)

HRID 2259985

反応式

HRID 2259985 の反応式
[CH2:1]([N:3]([CH2:11][CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[CH:5]=1)[CH3:2].[S:14](=[O:18])(=[O:17])([OH:16])[OH:15].[N:19](OC(C)C)=O.[H][H]>[C].[Pd].C(O)(C)C>[S:14]([OH:18])([OH:17])(=[O:16])=[O:15].[NH2:19][C:7]1[CH:8]=[CH:9][C:4]([N:3]([CH2:1][CH3:2])[CH2:11][CH2:12][OH:13])=[CH:5][C:6]=1[CH3:10]

参加物

7

反応物 4

HCID 1118Sulfuric Acid2 回HCID 70672-(N-ethyl-m-toluidino)ethanolHCID 10929Isopropyl nitriteHCID 178418361HCID 178418361、化合物

生成物 1

HCID 91579Ethanol, 2-((4-amino-3-methylphenyl)ethylamino)-, sulfate (1:1)収率 181.6%

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 3776Isopropanol溶媒2 回

反応条件

温度
10 °C

実験手順

With 89.6 g (0.5 mole) of N-ethyl-N-(β-hydroxyethyl)-m-toluidine was mixed 270 ml of 70% v/v isopropanol, and 24.5 g (0.25 mole) of sulfuric acid was added with cooling and stirring at 10° C. or lower. After 49.0 g (0.55 mole) of isopropyl nitrite was added dropwise at 10° C. or lower, the reaction was carried out at 2°-5° C. for another 4 hours. After completion of the reaction, hydrogenation was carried out at 40°-45° C. and at a hydrogen pressure of 3-5 kg/cm2 while adding the nitrosation reaction mixture to 270 ml of 70% v/v isopropanol containing 6.5 g of 5% palladium-carbon over a period of 1.5 hours. After completion of the hydrogenation reaction, the catalyst was filtered off and the filtrate was concentrated to dryness to remove the solvent. The residue was dissolved in 270 ml of 90% v/v ethanol with heating and 24.5 g (0.25 mole) of sulfuric acid was added at 45°-50° C. Then, the resulting mixture was cooled for 2 hours to carry out crystallization, and the crystals thus formed were collected by filtration at 3° C., washed with 100 ml of cold ethanol, and then dried to obtain 132.7 g of 4-amino-3-methyl-N-ethyl-N-(β-hydroxyethyl)aniline sulfate as white powder. Yield: 90.8%. Melting point: 154.6° C. The purity of 4-amino-3-methyl-N-ethyl-N-(β-hydroxyethyl)aniline sulfate was 100% as measured by HPLC, namely, no impurity was detected at all.

後処理

  1. additionwas added
  2. temperaturewith cooling
  3. customAfter completion of the reaction, hydrogenation
  4. additionwhile adding
  5. customAfter completion of the hydrogenation reaction
  6. filtrationthe catalyst was filtered off
  7. concentrationthe filtrate was concentrated to dryness
  8. customto remove the solvent
  9. dissolutionThe residue was dissolved in 270 ml of 90% v/v ethanol
  10. temperaturewith heating
  11. temperatureThen, the resulting mixture was cooled for 2 hours
  12. customcrystallization
  13. customthe crystals thus formed
  14. filtrationwere collected by filtration at 3° C.
  15. washwashed with 100 ml of cold ethanol
  16. customdried

出典と根拠

ORDレコード
ord-9707bd872024407fa1b83ebc28baefac
出典データセット
uspto-grants-1995_12
特許番号
US05475140

関連ノート

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