Nitric Acid → 2-(p-Nitrobenzyl)-4-(4-pyridyl)thiazole

HRID 4346

반응식

HRID 4346 반응식
[CH2:1]([C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[N+:24]([O-])([OH:26])=[O:25].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[N+:24]([C:5]1[CH:4]=[CH:3][C:2]([CH2:1][C:8]2[S:9][CH:10]=[C:11]([C:13]3[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=3)[N:12]=2)=[CH:7][CH:6]=1)([O-:26])=[O:25]

참가 물질

6

반응물 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 140969524-(2-Benzyl-1,3-thiazol-4-yl)pyridine

생성물 1

HCID 140969552-(p-Nitrobenzyl)-4-(4-pyridyl)thiazole수율 85.9%

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
10 °C

실험 절차

A solution of 2-benzyl-4-(4-pyridyl)thiazole (4.50 g, 0.018 mol) in chloroform (25 mL) was added dropwise to concentrated sulfuric acid (15 mL). The resulting mixture was cooled to 10° C. and fuming nitric acid (1.45 g, 0.97 mL) carefully added dropwise such that the reaction temperature did not exceed 40° C. The mixture was allowed to stir for thirty minutes, carefully neutralized with saturated sodium carbonate and the layers separated. The aqueous layer was reextracted with chloroform (2×25 mL) and the combined organic extracts were washed with brine (20 mL), dried over magnesium sulfate, and concentrated to afford a crude product (4.6 g). Several recrystallizations from hexane/ethyl acetate afforded pure 2-(p-nitrobenzyl)-4-(4-pyridyl)thiazole. mp. 140°-142° C.

후처리

  1. customdid not exceed 40° C
  2. customthe layers separated
  3. washthe combined organic extracts were washed with brine (20 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ed73af56968b4454b488f0c1be5537e4
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725606

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