Ethylamine → HCID 21937402, compound

HRID 1241977Notes

Reaction equation

HRID 1241977 reaction equation
[CH2:1]([NH2:3])[CH3:2].C1COCC1.Cl[C:10]1[CH:23]=[CH:22][C:13]([C:14]([NH:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])=[O:15])=[CH:12][C:11]=1[N+:24]([O-:26])=[O:25]>>[CH3:20][N:19]([CH3:21])[CH2:18][CH2:17][NH:16][C:14](=[O:15])[C:13]1[CH:22]=[CH:23][C:10]([NH:3][CH2:1][CH3:2])=[C:11]([N+:24]([O-:26])=[O:25])[CH:12]=1

Participants

4

Reactant 3

HCID 6341EthylamineHCID 8028TetrahydrofuranHCID 17611030HCID 17611030, compound

Product 1

HCID 21937402HCID 21937402, compoundYield 73%

Conditions

Temperature
65 °C

Procedure

To 2.0 M solution of ethylamine in THF (8 mL, 16 mmol) slowly added 4-chloro-N-(2-dimethylaminoethyl)-3-nitrobenzamide (0.40 g, 1.5 mmol). After heating at 65° C. for 16 h, the reaction mixture was cooled, concentrated and chromatographed (silica gel, MeOH/DCM, 3:22) to afford the title compound (0.30 g, 73%) as a yellow solid. 1H-NMR (CD3OD): δ 8.75 (1H, d), 8.32 (1H, br s), 7.98 (1H, dd), 7.08 (1H, d), 3.58–3.64 (3H, m), 3.43–3.51 (2H, m), 2.94 (2H, br t), 2.62 (6H, s), 1.35 (3H, t).

Workup

  1. temperaturethe reaction mixture was cooled
  2. concentrationconcentrated
  3. customchromatographed (silica gel, MeOH/DCM, 3:22)

Sources & evidence

ORD record
ord-b83695be6dc049e385d04febabd300c7
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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