2-Methyl-2-butanol → HCID 178453672, 화합물

HRID 613376

반응식

HRID 613376 반응식
[C:1]([NH:8][CH2:9][CH2:10][NH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.Cl[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N+:15]=1[O-:20].C([O-])(O)=O.[Na+].C(O)(CC)(C)C>C(Cl)Cl>[C:1]([NH:8][CH2:9][CH2:10][NH:11][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N+:15]=1[O-:20])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

참가 물질

6

반응물 4

HCID 64052-Methyl-2-butanolHCID 88478Chloride 2-chloropyridinium 1-oxideHCID 187201N-BOC-ethylenediamineHCID 516892Sodium Bicarbonate

생성물 1

HCID 178453672HCID 178453672, 화합물수율 89.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of mono-Boc-1,2-ethylenediamine (5.83 g, 36.39 mmole), 2-chloropyridine-N-oxide hydrochloride (7.25 g, 43.67 mmole), NaHCO3 (15.29 g, 182 mmole), and tert-amyl alcohol (36 mL) was heated at reflux. After 47 hr, the dark brown mixture was cooled, diluted with CH2Cl2 (100 mL), and suction filtered to remove insoluble materials. The filtrate was concentrated and reconcentrated from toluene. Silica gel chromatography (10% MeOH/CHCl3) gave impure title compound (8.23 g, 89%) as a yellow solid which was used without further purification: TLC (10% MeOH/CHCl3) Rf 0.42; 1H NMR (250, CDCl3) δ 8.16 (dd, J=6.5, 1.3 Hz, 1 H), 7.05-7.30 (m, 2 H), 6.68 (br d, J=8.6 Hz, 1 H), 6.50-6.65 (m, 1 H), 5.70-5.95 (m, 1 H), 3.35-3.60 (m, 4 H), 1.44 (s, 9 H); MS (ES) m/e 254 (M+H)+.

후처리

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperaturethe dark brown mixture was cooled
  4. filtrationfiltered
  5. customto remove insoluble materials
  6. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-14ee808ca3384c56bd282f6d7041f04e
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008213

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