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

HRID 2052512노트

반응식

HRID 2052512 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e72014ae38674455b8b03b757c681c64
출처 데이터셋
uspto-grants-1980_01
특허 번호
US04185115

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