Triethylamine → N-[2-[(4-Methyl-2-pyridyl)amino]ethyl]methanesulfonamide

HRID 631814Notes

Reaction equation

HRID 631814 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][CH2:10][NH2:11])[CH:3]=1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][CH2:10][NH:11][S:20]([CH3:19])(=[O:22])=[O:21])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10034794N-(4-methylpyridin-2-yl)ethane-1,2-diamine

Product 1

HCID 61724432N-[2-[(4-Methyl-2-pyridyl)amino]ethyl]methanesulfonamideYield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of N-(4-methyl-2-pyridyl)ethane-1,2-diamine (683 mg, 4.52 mmol) in dichloromethane (25 ml) were added triethyl amine (1.26 ml, 9.06 mmol) followed by methanesulfonyl chloride (370 μl, 4.78 mmol). The mixture was stirred at room temperature for two hours and washed with saturated sodium bicarbonate solution. The organic phase was dried over sodium sulfate and concentrated to give 1.04 g of a yellow oil (4.57 mmol, 95%) MS(ESI) m/z=230.1 [M+1]+.

Workup

  1. washwashed with saturated sodium bicarbonate solution
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-df98dda310a04dda97802fd56cae038a
Source dataset
uspto-grants-2016_04
Patent number
US09321724B2

Reaction notes

Loading…