Nitroethane → tert-Butyl 6-cyano-2-pyridylmethylcarbamate

HRID 748170노트

반응식

HRID 748170 반응식
C[N+:2]([O-])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12]N=1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].C[Si](C#[N:22])(C)C.CN(C)C(Cl)=O.[N+:29]([CH2:32][CH3:33])([O-])=O>>[C:32]([C:33]1[N:22]=[C:15]([CH2:10][NH:2][C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6])[CH:14]=[CH:13][CH:12]=1)#[N:29]

참가 물질

5

반응물 4

HCID 6587NitroethaneHCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 86596460tert-butyl methyl(2-pyridyl)carbamate N-oxide

생성물 1

HCID 22939432tert-Butyl 6-cyano-2-pyridylmethylcarbamate수율 77%

실험 절차

A mixture of tert-butyl methyl(2-pyridyl)carbamate N-oxide (14.1 g, 63 mmol), trimethylsilyl cyanide (12.5 g, 126 mmol), N,N-dimethylcarbamoyl chloride (13.5 g, 125 mmol) and nitroethane (120 ml) was stirred at room temperature for 48 hrs. The reaction mixture was concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography, eluted with hexane-ethyl acetate (10:1, v/v) and recrystallized from ethyl acetate-hexane to give the titled compound (11.3 g, 77%).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washeluted with hexane-ethyl acetate (10:1
  3. customv/v) and recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-9dee629b34e845b99c756c47360cd8e1
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399759B2

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