tert-butyl N-(4-aminobutyl)carbamate → Tert-butyl 4-(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)butylcarbamate

HRID 1070778노트

반응식

HRID 1070778 반응식
N[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[Cl:14][C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[C:19](Cl)[C:18]([CH3:25])=[C:17]([CH3:26])[N:16]=1.CN(C)C=O.C(N(CC)CC)C>C(OCC)(=O)C>[Cl:14][C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[C:19]([CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C:18]([CH3:25])=[C:17]([CH3:26])[N:16]=1

참가 물질

6

반응물 4

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 6228DimethylformamideHCID 8471TriethylamineHCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridine

생성물 1

HCID 21973830Tert-butyl 4-(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)butylcarbamate수율 79.8%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Tert-butyl 4-aminobutylcarbamate (60 g, 339 mmol) was slowly added to a mixture of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (50 g, 226 mmol), anhydrous N,N-dimethylformamide (500 mL) and triethylamine (50 mL, 339 mmol). The reaction mixture was allowed to stir overnight and then it was concentrated under reduced pressure to provide an oil. The oil was dissolved in ethyl acetate and then washed with water. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure to provide a dark oil. This material was purified by column chromatography (silica gel eluting with 40/60 ethyl acetate/hexanes) to provide 64.5 g of tert-butyl 4-(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)butylcarbamate as a bright orange oil which solidified on standing.

후처리

  1. concentrationit was concentrated under reduced pressure
  2. customto provide an oil
  3. washwashed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto provide a dark oil
  7. customThis material was purified by column chromatography (silica gel eluting with 40/60 ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-e09bfa8abdff4282ad5b79e2e340d8c1
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903113B2

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