Triethylamine → HCID 11404780, compound

HRID 1058505Notes

Reaction equation

HRID 1058505 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

HCID 11404780HCID 11404780, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 3283Diethyl EtherSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-80dab15af840495eb8a236a03f46767b
Source dataset
uspto-grants-2003_02
Patent number
US06517836B1

Reaction notes

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