4-Methoxybenzoic Acid → N,N-Diethyl-para-anisamide

HRID 507681Notes

Reaction equation

HRID 507681 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.[CH2:12]([NH:14][CH2:15][CH3:16])[CH3:13].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH2:12]([N:14]([CH2:15][CH3:16])[C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=1)[CH3:13]

Participants

5

Reactant 3

HCID 74784-Methoxybenzoic AcidHCID 8021DiethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 231459N,N-Diethyl-para-anisamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Methoxybenzoic acid (6 g, 39 mmol) was treated with diethylamine (4.45 mL, 43 mmol), TBTU (15 g, 46.8 mmol), disopropylethylamine (10.2 mL, 58.5 mmol) in DMF (40 mL). The mixture was stirred at ambient temperature overnight. The reaction was poured into ice water and the resulting mixture extracted several times with ethyl acetate. The organic layer was washed with a solution of saturated sodium bicarbonate, water and then brine. The organic layer was then dried with sodium sulfate, concentrated and purified by flash chromatography using a gradient of 30 to 70% ethyl acetate in hexanes to obtain a brown oil. Yield=7.8 g. MS (M+H)+ 208.

Workup

  1. extractionthe resulting mixture extracted several times with ethyl acetate
  2. washThe organic layer was washed with a solution of saturated sodium bicarbonate, water
  3. dry with materialThe organic layer was then dried with sodium sulfate
  4. concentrationconcentrated
  5. custompurified by flash chromatography
  6. customto obtain a brown oil

Sources & evidence

ORD record
ord-654258fce488449da95884f715ebd58b
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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