Benzocaine → 4-{[2-(4-Fluorophenyl)ethyl]amino}benzoic acid

HRID 1703098노트

반응식

HRID 1703098 반응식
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1.[NH2:11][C:12]1[CH:22]=[CH:21][C:15]([C:16]([O:18]CC)=[O:17])=[CH:14][CH:13]=1.[I-].[K+].CN(C)P(N(C)C)(N(C)C)=O>O>[F:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][NH:11][C:12]2[CH:22]=[CH:21][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 2337BenzocaineHCID 4875Potassium IodideHCID 12679HexamethylphosphoramideHCID 676221-(2-Chloroethyl)-4-fluorobenzene

생성물 1

HCID 130796804-{[2-(4-Fluorophenyl)ethyl]amino}benzoic acid

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 15.8 g. of 1-(2-chloroethyl)-4-fluorobenzene, 33 g. of ethyl p-aminobenzoate, 16.6 g. of potassium iodide and 100 ml. of hexamethylphosphoramide is heated at 95° C. for 15 hours. The mixture is poured into water and extracted with ether. The ether extracts are washed with water, dried over magnesium sulfate and concentrated in vacuo to an oil. To the oil is added 200 ml. of ethanol-water (9:1) and 21 g. of potassium hydroxide and the mixture is refluxed for 3.5 hours. The mixture is acidified with concentrated hydrochloric acid, diluted with water, cooled and filtered to give gray crystals. Recrystallization from ethanol gives light gray crystals, m.p. 161°-163° C.

후처리

  1. additionA mixture of 15.8 g
  2. extractionextracted with ether
  3. washThe ether extracts are washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo to an oil
  6. additionTo the oil is added 200 ml
  7. temperatureof potassium hydroxide and the mixture is refluxed for 3.5 hours
  8. additiondiluted with water
  9. temperaturecooled
  10. filtrationfiltered
  11. customto give gray crystals
  12. customRecrystallization from ethanol
  13. customgives light gray crystals, m.p. 161°-163° C.

출처 및 근거

ORD 기록
ord-5a3dada79bf749a89e25c60eb065b198
출처 데이터셋
uspto-grants-1982_09
특허 번호
US04350822

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