Dimethylformamide → 5,6-Dichloro-N-ethylnicotinamide

HRID 502540Notes

Reaction equation

HRID 502540 reaction equation
[ClH:1].C(N)C.CN(C)C=[O:8].C([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])C.[ClH:17].[CH3:18][N:19](C)[CH2:20][CH2:21][CH2:22]N=C=NCC>ClCCl>[Cl:1][C:21]1[C:20]([Cl:17])=[N:19][CH:18]=[C:16]([CH:22]=1)[C:15]([NH:12][CH2:13][CH3:14])=[O:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 201201335,6-Dichloro-N-ethylnicotinamideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round bottomed flask was charged with 5,6-dichlorornicotic acid (30 g, 156 mmol), ethylamine HCl salt (14 g, 170 mmol), dimethylformamide (300 ml), dichloromethane (100 ml), triethylamine (26.1 ml, 187 mmol), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (32.9 g, 170 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo, the residue was dissolved in ethyl acetate (500 mL) and was washed with 1N HCl (2×), saturated aqueous sodium bicarbonate (1×), brine (1×), and dried over magnesium sulfate. The solution was filtered and concentrated in vacuo to provide the desired 5,6-Dichloro-N-ethyl-nicotinamide 2 (29 g, 85%). MS: M+H=219.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (500 mL)
  3. washwas washed with 1N HCl (2×), saturated aqueous sodium bicarbonate (1×), brine (1×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d6eecdb230794df0985b83146d26e8ca
Source dataset
uspto-grants-2010_08
Patent number
US07776862B2

Reaction notes

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