Triethylamine → HCID 11404780, 화합물

HRID 1058505노트

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HRID 1058505 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

HCID 11404780HCID 11404780, 화합물수율 47%

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 3283Diethyl Ether용매2회HCID 24386Thionyl Chloride용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-80dab15af840495eb8a236a03f46767b
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06517836B1

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