Triethylamine → N-(2,2-diethoxyethyl)-3-methoxy-2-nitrobenzamide

HRID 577486

反応式

HRID 577486 の反応式
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[C:10]([N+:18]([O-:20])=[O:19])=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O.[CH2:21]([O:23][CH:24]([O:27][CH2:28][CH3:29])[CH2:25][NH2:26])[CH3:22].C(N(CC)CC)C>ClCCl.CN(C)C=O>[CH2:21]([O:23][CH:24]([O:27][CH2:28][CH3:29])[CH2:25][NH:26][C:12](=[O:14])[C:11]1[CH:15]=[CH:16][CH:17]=[C:9]([O:8][CH3:7])[C:10]=1[N+:18]([O-:20])=[O:19])[CH3:22]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 695242,2-DiethoxyethylamineHCID 786323-Methoxy-2-nitrobenzoic acid

生成物 1

HCID 86723712N-(2,2-diethoxyethyl)-3-methoxy-2-nitrobenzamide収率 97%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

Oxalyl chloride (34 mL, 0.395 mol) was added to a solution of 3-methoxy-2-nitrobenzoic acid (60 g, 0.305 mol) in dry dichloromethane (600 mL), followed by N,N-dimethylformamide (0.6 mL, 7.8 mmol), which initiates mild gas evolution. The mixture was stirred at room temperature for two hours, then concentrated under vacuum to remove volatiles. The crude acid chloride was dissolved in dry dichloromethane (150 mL) then added dropwise to a cooled (5° C.) solution of aminoacetaldehyde diethylacetal (48 mL, 0.33 mol) and triethylamine (52 mL, 0.374 mol) in dry dichloromethane (250 mL). The mixture was stirred at room temperature for two hours, then washed with saturated aqueous sodium bicarbonate (2×100 mL) and brine (100 mL). The organics were dried over sodium sulfate and concentrated to give N-(2,2-diethoxyethyl)-3-methoxy-2-nitrobenzamide (296a, 92 g, 97% yield) as a yellow solid. MS: 335 [M+1].

後処理

  1. concentrationconcentrated under vacuum
  2. customto remove volatiles
  3. dissolutionThe crude acid chloride was dissolved in dry dichloromethane (150 mL)
  4. additionthen added dropwise to
  5. stirringThe mixture was stirred at room temperature for two hours
  6. washwashed with saturated aqueous sodium bicarbonate (2×100 mL) and brine (100 mL)
  7. dry with materialThe organics were dried over sodium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-3dd1029fa0c342ca8dc5e1dce0bb5721
出典データセット
uspto-grants-2015_05
特許番号
US09040515B2

関連ノート

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