1-Hydroxybenzotriazole → 2-(3,4-Dimethoxyphenoxy)-N-methoxy-N-methylacetamide

HRID 710053Notes

Reaction equation

HRID 710053 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[O:6][CH2:7][C:8]([OH:10])=O.Cl.[CH3:17][NH:18][O:19][CH3:20].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CCN(CC)CC.O.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[O:6][CH2:7][C:8]([N:18]([O:19][CH3:20])[CH3:17])=[O:10]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 218358392-(3,4-Dimethoxyphenoxy)acetic acid

Product 1

HCID 867067662-(3,4-Dimethoxyphenoxy)-N-methoxy-N-methylacetamideYield 78.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of CHCl3 (100 mL) with 2-(3,4-dimethoxyphenoxy)acetic acid (4.244 g), N,O-dimethylhydroxyamine hydrochloride (2.341 g), WSC.HCl (4.984 g) and HOBt.H2O (3.513 g), Et3N (3.62 mL) was added and the mixture was stirred at room temperature for 20 hours. The reaction mixture was concentrated, H2O (400 mL) was added, and the organic layer extracted with AcOEt (500 mL) was washed successively with saturated aqueous sodium dicarbonate (400 mL), water (400 mL) and brine (400 mL), dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by silica gel chromatography (AcOEt) to give the titled compound (4.01 g, pale brown oil.)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionH2O (400 mL) was added
  3. extractionthe organic layer extracted with AcOEt (500 mL)
  4. washwas washed successively with saturated aqueous sodium dicarbonate (400 mL), water (400 mL) and brine (400 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude product, which
  9. customwas further purified by silica gel chromatography (AcOEt)

Sources & evidence

ORD record
ord-40561949f609483b93720d9ec89263ca
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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