N,N-Dimethylethylenediamine → HCID 17611030, compound

HRID 1241976Notes

Reaction equation

HRID 1241976 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][NH2:18].C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:18][CH2:17][CH2:16][N:15]([CH3:19])[CH3:14])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 1234774-Chloro-3-nitrobenzoyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 17611030HCID 17611030, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a chilled solution (−10° C.) of 4-chloro-3-nitrobenzoyl chloride (0.92 g, 4.2 mmol) in anhydrous THF (20 mL) added dropwise a solution of N,N-dimethylethylenediamine (0.44 mL, 4.0 mmol) in THF (20 mL). After stirring 30 min combined with a 1:1 mixture of ice and saturated NaHCO3 (50 mL) and then extracted with EtOAc (3×80 mL). The combined organic layers were dried over anhydrous Na2SO4, concentrated and chromatographed (silica gel, MeOH/DCM, 3:22) to yield the title compound (0.40 g, 37%) as a pale yellow solid. 1H-NMR (CDCl3): δ 8.28 (1H, d), 7.96 (1H, dd), 7.63 (1H, d), 6.98 (1H, br s), 3.54 (2H, m), 2.56 (2H, t), 2.30 (6H, s)

Workup

  1. extractionextracted with EtOAc (3×80 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customchromatographed (silica gel, MeOH/DCM, 3:22)

Sources & evidence

ORD record
ord-4c5ebcd87c9141c6ae61a511370e1be6
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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