Trimethyl orthoformate → 1-((4-methoxyphenyl)methyl)-1H-1,2,3,4-tetrazole

HRID 842755노트

반응식

HRID 842755 반응식
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[CH3:11]OC(OC)OC.[N-:18]=[N+:19]=[N-:20].[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:8]2[CH:11]=[N:20][N:19]=[N:18]2)=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 9005Trimethyl orthoformateHCID 33557Sodium AzideHCID 754524-Methoxybenzylamine

생성물 1

HCID 109978051-((4-methoxyphenyl)methyl)-1H-1,2,3,4-tetrazole

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
80 °C

실험 절차

The mixture of 4-methoxybenzylamine (27 g), trimethylorthoformate (52.4 ml), sodium azide (19.2 g) and acetic acid (176 ml) was stirred at 80° C. for 14 h. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in water and extracted with ethyl acetate. The extract was washed with a 1 N aqueous solution of hydrochloric acid, water, a saturated aqueous solution of sodium hydrocarbonate and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to give the title compound (17.6 g) having the following physical data.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with a 1 N aqueous solution of hydrochloric acid, water
  5. dry with materiala saturated aqueous solution of sodium hydrocarbonate and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-ae55c629348c466aaa8022e2ef0c899c
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06376484B1

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