4-Toluenesulfonyl chloride → HCID 178463249、化合物

HRID 1155542ノート

反応式

HRID 1155542 の反応式
[Na].[CH2:2]([NH:4][C:5]1[CH:10]=[C:9]([C:11](=[N:13]O)[CH3:12])[CH:8]=[CH:7][N:6]=1)[CH3:3].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[O-]CC.[K+].[S-:30][C:31]#[N:32].[K+].C(=O)([O-])[O-].[Na+].[Na+]>O.C(OCC)C.C(O)C>[CH2:2]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[N:13]=[C:31]([SH:30])[NH:32][CH:12]=2)[CH:8]=[CH:7][N:6]=1)[CH3:3]

参加物

10

反応物 6

HCID 73974-Toluenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 516872Potassium thiocyanateHCID 5360545SodiumHCID 23670592Potassium ethoxideHCID 136359197HCID 136359197、化合物

生成物 1

HCID 178463249HCID 178463249、化合物

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

To 20 ml. of absolute ethanol containing 240 mg. of dissolved sodium was added 1.79 g. (10 mmoles) of 1-(2-ethylamino-4-pyridyl)-1-ethanone oxime, and the mixture stirred until homogeneous (~5 minutes). p-Toluenesulfonyl chloride (2.04 g., 10.7 mmole) was added and the mixture stirred at room temperature under nitrogen for 1 hour. the mixture was added to a solution of potassium ethoxide (prepared by dissolving 430 mg. of potassium in 20 ml. of absolute ethanol) and the resulting mixture allowed to stir at room temperature for 0.5 hour. The resulting gelatinous suspension was diluted with 100 ml. of diethyl ether and stirred at room temperature for 30 minutes. The reaction was filtered through celite and the filtrate was concentrated. The residue was dissolved in 100 ml. of ether and any remaining solids filtered. The ether solution was extracted with 2 N hydrochloric acid (4×15 ml.) and the combined acid extracts concentrated to give a yellow solid. The residue was dissolved in 30 ml. of water containing 1.94 g. (20 mmoles) of potassium thiocyanate and the solution heated on a steam bath for 2 hours. After cooling, the mixture was made basic with sodium sodium carbonate and the precipitate filtered, washed with water and dried, 1.27 g. (58%), m.p. >260° C.

後処理

  1. stirringto stir at room temperature for 0.5 hour
  2. additionThe resulting gelatinous suspension was diluted with 100 ml
  3. filtrationThe reaction was filtered through celite
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in 100 ml
  6. filtrationof ether and any remaining solids filtered
  7. extractionThe ether solution was extracted with 2 N hydrochloric acid (4×15 ml.)
  8. concentrationthe combined acid extracts concentrated
  9. customto give a yellow solid
  10. dissolutionThe residue was dissolved in 30 ml
  11. temperatureAfter cooling
  12. filtrationthe precipitate filtered
  13. washwashed with water
  14. customdried

出典と根拠

ORDレコード
ord-c3bd15bed95a4d4080cf662c43c6e9ff
出典データセット
uspto-grants-1981_11
特許番号
US04302464

反応ノート

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