Diethylamine → N,N-diethyl-3-methoxybenzamide

HRID 2359651Notes

Reaction equation

HRID 2359651 reaction equation
[C:1]([OH:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.CN(C(ON1N=N[C:22]2C=[CH:24][CH:25]=[N:26][C:21]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.C(NCC)C>CN(C=O)C.O>[CH2:25]([N:26]([CH2:21][CH3:22])[C:1](=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1)[CH3:24]

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 114613-Methoxybenzoic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 669438N,N-diethyl-3-methoxybenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of m-anisic acid (0.5 g; 3.29 mmol) and HATU (1.4 g; 3.68 mmol) in DMF (5 mL) was added N,N-diisopropylethylamine (2 mL; 11.48 mmol). The reaction was stirred at room temperature for 30 min. Diethylamine (0.377 mL; 3.62 mmol) was added to the reaction. The mixture was stirred at room temperature for 1.5 d, diluted with H2O (5 mL), and extracted with EtOAc (2×5 mL). The organic layer was dried over MgSO4 and concentrated to afford Compound 15a. The crude product was used in the next reaction without further purification. MS: m/z 208.2 (M+H)+.

Workup

  1. stirringThe mixture was stirred at room temperature for 1.5 d
  2. extractionextracted with EtOAc (2×5 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-04d4ebe63e3d4e0f925de11bc81a33e7
Source dataset
uspto-grants-2014_04
Patent number
US08685990B2

Reaction notes

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