Dimethylformamide → HCID 86664842, 화합물

HRID 2365237노트

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HRID 2365237 반응식
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:4]=[N:3]1.[Li]CCCC.CN([CH:21]=[O:22])C.[Cl-].[NH4+]>C1COCC1>[CH3:1][N:2]1[C:6]([CH:21]=[O:22])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:4]=[N:3]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 57746172HCID 57746172, 화합물HCID 178418339Butyllithium

생성물 1

HCID 86664842HCID 86664842, 화합물수율 91%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-75 °C

실험 절차

To a solution of 2-(1-methyl-1H-[1,2,3]triazol-4-yl)-pyridine (3.52 g, 22 mmol) in THF (112 mL) was added n-BuLi (1.6 M in hexane, 16.5 mL, 4.96 mmol) dropwise at −75° C. and under Ar. The resulted light brown suspension was stirred at −75° C. for 1 h. Then DMF (2.20 mL, 29 mmol) was added dropwise at −75° C. and the yellow solution was allowed to warm up to room temperature over 1 h. The mixture was then poured into saturated ammonium chloride solution and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) afforded the title compound (3.75 g, 91%) as a white solid. MS: m/e=188.0 [M]+.

후처리

  1. temperatureto warm up to room temperature over 1 h
  2. extractionextracted with ethyl acetate
  3. washthe combined organic extracts washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography (silica, 0 to 100% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-8f35a20d2cbe46eda1964ec8b8f0f3eb
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697696B2

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