Ethanol → Ethyl 4-{[2-(thiophen-2-yl)ethyl]amino}benzoate

HRID 1389777ノート

反応式

HRID 1389777 の反応式
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.CS(O[CH2:18][CH2:19][C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)(=O)=O.CN(C)P(N(C)C)(N(C)C)=O.C(O)C>O>[S:21]1[CH:22]=[CH:23][CH:24]=[C:20]1[CH2:19][CH2:18][NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1

参加物

6

反応物 4

HCID 702EthanolHCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 30477232-(2-Thienyl)ethyl methanesulphonate

生成物 1

HCID 13079686Ethyl 4-{[2-(thiophen-2-yl)ethyl]amino}benzoate

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 33.0 g. of ethyl p-aminobenzoate, 21.8 g. of 2-(2-thienyl)ethanol O-methanesulfonate (prepared as described in Example 49) and 100 ml. of hexamethylphosphoramide is heated in an oil bath at 125° C. for 16 hours. The mixture is chilled, diluted with 15 ml. of ethanol and 150 ml. of water. The mixture is extracted with ether and the ether extracts washed with water, dried over magnesium sulfate and concentrated in vacuo to give a crude oil. A sample of this oil is chromatographed over silica gel and the fractions containing the product are combined and recrystallized from hexane to give ethyl 4-[2-(2-thienyl)ethylamino]benzoate as yellow-tan crystals, m.p. 93°-95° C.

後処理

  1. additionA mixture of 33.0 g
  2. temperatureThe mixture is chilled
  3. additiondiluted with 15 ml
  4. extractionThe mixture is extracted with ether
  5. washthe ether extracts washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give a crude oil
  9. customA sample of this oil is chromatographed over silica gel
  10. additionthe fractions containing the product
  11. customrecrystallized from hexane

出典と根拠

ORDレコード
ord-f13e6b40db6b463886c9d7d55467c3d8
出典データセット
uspto-grants-1981_01
特許番号
US04246275

反応ノート

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