Water → HCID 59530560, compound

HRID 1518042Notes

Reaction equation

HRID 1518042 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([N+:11]([O-:13])=[O:12])=[C:4]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH:3]=1.[CH3:19][O:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24].O>N1C=CC=CC=1>[CH2:15]([N:14]([CH2:17][CH3:18])[C:4]1[C:5]([N+:11]([O-:13])=[O:12])=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([NH:1][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=2[O:20][CH3:19])[CH:3]=1)[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 889692-Methoxybenzoyl chlorideHCID 50994291HCID 50994291, compound

Product 1

HCID 59530560HCID 59530560, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1-amino-3-diethylamino-4,6-dinitrobenzene (508 mg, 2.0 mmol) in 5 mL of pyridine, 2-methoxybenzoyl chloride (680 mg, 4.0 mmol) was added. After refluxing for 5 h, 50 mL of water was added to the reaction mixture, and the precipitate was collected by filtration and washed with 200 mL of water. Recrystallization from dichloromethane and methanol gave the desired product (622 mg, 80% yield) as a yellow solid: 1H-NMR (300 MHz, CDCl3) δ 1.29 (t, 6H, J=7.2 Hz), 3.39 (q, 4H, J=7.2 Hz), 4.13 (s, 3H), 7.07 (d, 1H, J=8.1), 7.11 (t, 1H, J=9.8 Hz), 7.55 (t, 1H, J=7.8 Hz), 8.23 (d, 1H, J=8.1 Hz), 8.83 (s, 1H), 8.98 (s, 1H); ESI MS m/z 389.1 [M+H]+.

Workup

  1. temperatureAfter refluxing for 5 h
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with 200 mL of water
  4. customRecrystallization from dichloromethane and methanol

Sources & evidence

ORD record
ord-68a13016fd194f24958e5c7a297c68e8
Source dataset
uspto-grants-2012_07
Patent number
US08232410B2

Reaction notes

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