Dimethylamine, hydrochloride → 2,6-dimethoxy-N,N-dimethylbenzamide

HRID 488687Notes

Reaction equation

HRID 488687 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:4]=1[C:5](O)=[O:6].Cl.[CH3:15][NH:16][CH3:17].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:4]=1[C:5]([N:16]([CH3:17])[CH3:15])=[O:6]

Participants

8

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 151092,6-Dimethoxybenzoic AcidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 32670112,6-dimethoxy-N,N-dimethylbenzamideYield 56.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,6-dimethoxybenzoic acid (102 mg, 0.56 mmol), dimethylamine hydrochloride (91 mg, 1.12 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (234 mg, 0.73 mmol) and diisopropylethylamine (390 μL, 2.24 mmol) in DMF (1 mL) was stirred at ambient temperature overnight. The reaction mixture was taken up in ethyl acetate (50 mL) and aqueous. NaHCO3(50 mL). The organic phase was washed with brine (2×50 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified on silica gel eluting with ethyl acetate to provide titled compound (66 mg). MS (APCI(+)) m/e 210 (M+H)+.

Workup

  1. washThe organic phase was washed with brine (2×50 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-25dbf8b7744c4b34be03f6ece7671b7d
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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