Dimethylamine, hydrochloride → 4-iodo-N,N-dimethylbenzamide

HRID 1643740Notes

Reaction equation

HRID 1643740 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][CH:3]=1.[CH3:11][N:12](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:13].F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.CNC>CN(C=O)C.O>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:12]([CH3:13])[CH3:11])=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 120854-Iodobenzoic 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 8799334-iodo-N,N-dimethylbenzamideYield 68.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-iodobenzoic acid (2.0 g, 8.0 mmol), HATU (4.6 g, 12.0 mmol) and DIPEA (1.6 g, 12.0 mmol) in DMF (30 mL) was stirred for 1 h. Then, dimethylamine hydrochloride (0.98 mg, 12.0 mmol) was added. The resulting solution was stirred overnight. The reaction was monitored by TLC (petroleum ether/EtOAc 2:1). The reaction mixture was poured into water (30 mL) and extracted with EtOAc (40 mL×3). The organic layer was washed with brine (20 mL×2), dried over Na2SO4 and concentrated. The product was purified by silica gel column chromatography using petroleum ether/EtOAc (4:1) to afford the desired compound (1.5 g, 60%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.75 (d, 2H), 7.16 (d, 2H), 3.15-2.97 (d, 6H).

Workup

  1. extractionextracted with EtOAc (40 mL×3)
  2. washThe organic layer was washed with brine (20 mL×2)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e8049bcf6e4e472796a230c9bc4fa3fe
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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