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

HRID 1060666ノート

反応式

HRID 1060666 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-eb43692773ba48158f11a235e4fbcf5a
出典データセット
uspto-grants-2003_02
特許番号
US06525064B1

反応ノート

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