Benzocaine → 4-(1H-1,2,3,4-tetrazol-1-yl)benzoic acid

HRID 68786노트

반응식

HRID 68786 반응식
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][CH:3]=1.[CH2:13](OC(OCC)OCC)C.[N-:23]=[N+:24]=[N-:25].[Na+]>C(O)(=O)C>[N:1]1([C:2]2[CH:12]=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH:13]=[N:25][N:24]=[N:23]1

참가 물질

5

반응물 3

HCID 2337BenzocaineHCID 31214Ethyl orthoformateHCID 33557Sodium Azide

생성물 1

HCID 6741614-(1H-1,2,3,4-tetrazol-1-yl)benzoic acid

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a solution of ethyl 4-aminobenzoate (1.65 g) in acetic acid (20 mL) is added triethylorthoformate (8 mL) and sodium azide (1.17 g) and the solution is heated at reflux for 4 h. After cooling and removing acetic acid in vacuo, water and dichloromethane are added and the organic layer is separated and dried (MgSO4) and concentrated. The crude ester is dissolved in methanol (30 mL) and 4 M aqueous NaOH solution (3 mL) is added and the solution is stirred at room temperature for 2 h. The mixture is neutralized with 6 M aqueous HCl, concentrated and then acidified with 6 M aqueous HCl. The precipitate is filtered off washing with water and dried by suction to give the title compound.

후처리

  1. temperaturethe solution is heated
  2. temperatureat reflux for 4 h
  3. temperatureAfter cooling
  4. customremoving acetic acid in vacuo, water and dichloromethane
  5. additionare added
  6. customthe organic layer is separated
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. dissolutionThe crude ester is dissolved in methanol (30 mL)
  10. addition4 M aqueous NaOH solution (3 mL) is added
  11. concentrationconcentrated
  12. filtrationThe precipitate is filtered off
  13. washwashing with water
  14. customdried by suction

출처 및 근거

ORD 기록
ord-923db62779d043b4a03f4aef670841ea
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822471B2

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