Dimethylamine → Methyl 4-(dimethylcarbamoyl)benzoate

HRID 1808885Notes

Reaction equation

HRID 1808885 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][CH:6]=1)=[O:4].[CH3:14][N:15](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:16].F[P-](F)(F)(F)(F)F.CNC.C(N(CC)CC)C>C1COCC1>[CH3:14][N:15]([CH3:16])[C:9]([C:8]1[CH:12]=[CH:13][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1)=[O:10]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 15513Monomethyl terephthalateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 11106558Methyl 4-(dimethylcarbamoyl)benzoateYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a soln. of 4-(methoxycarbonyl)benzoic acid (100 mg, 0.555 mmol) in THF (5 ml) was added HATU (211 mg, 0.555 mmol), dimethylamine (0.278 ml, 0.555 mmol) and triethylamine (0.077 ml, 0.555 mmol) at r.t. The mixture was stirred at r.t for 4 hrs. Evaporated to remove the solvent. The residue was dissolved in EtOAc (10 ml), washed w/water (3×), brine. Dried (Na2SO4), and evaporated to afford methyl 4-(dimethylcarbamoyl)benzoate (100 mg, 0.458 mmol, 83% yield) as solid. 1H-NMR (CD3OD, 500 MHz): δ 8.10 (1H, d, J=6.4 Hz), 7.55 (1H, d, J=6.4 Hz), 3.94 (3H, s), 3.13 (3H, s), 2.99 (3H, s). m/e (M+H): 208.1

Workup

  1. customEvaporated
  2. customto remove the solvent
  3. dissolutionThe residue was dissolved in EtOAc (10 ml)
  4. washwashed w/water (3×), brine
  5. dry with materialDried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-67be1f4bfb1c4990b9c4ab6b518c4ab2
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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