Triethylamine → HCID 11404780、化合物

HRID 1058505ノート

反応式

HRID 1058505 の反応式
[Cl:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.Cl.[NH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22].CCN(CC)CC>O=S(Cl)Cl.CN(C=O)C.CCOCC>[Cl:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([NH:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[O:9]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 37278605-Chloro-2,4-dinitrobenzoic acid

生成物 1

HCID 11404780HCID 11404780、化合物収率 47%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 3283Diethyl Ether溶媒2 回HCID 24386Thionyl Chloride溶媒

実験手順

A solution of 5-chloro-2,4-dinitrobenzoic acid (10.0 g, 40 mmol) in SOCl2 (100 mL) containing DMF (2 drops) was heated under reflux for 5 h, and then concentrated to dryness and azeotroped with benzene. A solution of the resulting crude acid chloride in Et2O was added to a vigorously-stirred suspension of methyl 3-aminopropanoate hydrochloride (6.22 g, 44 mmol) and Et3N (13.9 mL, 100 mmol) in Et2O (100 mL). after stirrign for 30 min, the resulting precipitate was filtered off, washed well with water, and recrystallized from EtOAc/petroleum ether to give 5-chloro-N-[2-(methoxycarbonyl)ethyl]-2,4-dinitrobenzamide (6.24 g, 47%), mp 139-141° C. 1H NMR [(CD3)2SO] δ8.98 (t, J=5.6 Hz, 1H, CONH), 8.83 (s, 1H, H-3), 8.09 (s, 1H, H-6), 3.63 (s, 3H, OCH3), 3.47 (dt, J=6.7, 5.6 Hz, 2H, CONCH2), 2.61 (t, J=6.7 Hz, 2H, CH2CO2CH3) Anal. Calcd for C11H10ClN3O7. C, 39.84;H, 3.04; N, 12.67, Cl, 10 69. Found: C, 40.07;H, 2.79; N, 12 55; Cl, 10.92%.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 5 h
  3. concentrationconcentrated to dryness
  4. customazeotroped with benzene
  5. filtrationthe resulting precipitate was filtered off
  6. washwashed well with water
  7. customrecrystallized from EtOAc/petroleum ether

出典と根拠

ORDレコード
ord-80dab15af840495eb8a236a03f46767b
出典データセット
uspto-grants-2003_02
特許番号
US06517836B1

反応ノート

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