Iodine → N-methyl-3-iodoisonicotinamide

HRID 1975949노트

반응식

HRID 1975949 반응식
[CH3:1][NH:2][C:3](=[O:10])[C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.CN(C)CCN(C)C.C([Li])CCC.[I:24]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1.CCCCCC.O>[I:24][C:9]1[CH:8]=[N:7][CH:6]=[CH:5][C:4]=1[C:3]([NH:2][CH3:1])=[O:10]

참가 물질

9

반응물 5

HCID 807IodineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 24477Sodium ThiosulfateHCID 967071-MethylisonicotinamideHCID 178418339Butyllithium

생성물 1

HCID 22000069N-methyl-3-iodoisonicotinamide수율 39.5%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

To a solution of 1.36 g (10 mmol) N-methyl-isonicotin-amide in 20 ml tetrahydrofuran and 4.5 ml (30 mmol) N,N,N′,N′-tetramethylethylenediamine at −70° C. were added 25 ml (40 mmol) 1.6 M n-butyl lithium solution in hexane. After stirring for 2 h at −10 to 0° C. a solution of 7.6 g iodine in 20 ml tetrahydrofuran was added dropwise at −70° C. Stirring was continued for 1 h at room temperature and 100 ml saturated sodium thiosulfate solution in water were added. The aqueous layer was separated and washed twice with ethyl acetate. The combined organic layers were washed with 1 N sodium hydroxide solution, brine, dried (magnesium sulfate) and evaporated. The residue was purified by chromatography to give 1.035 g (39%) of the title compound as white crystals. M.p. 132-133° C.

후처리

  1. additionwas added dropwise at −70° C
  2. customThe aqueous layer was separated
  3. washwashed twice with ethyl acetate
  4. washThe combined organic layers were washed with 1 N sodium hydroxide solution, brine
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. customThe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-727e8929052b4af38b0c41688701240e
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06225316B1

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