Triethylamine → HCID 1484598, compound

HRID 842748Notes

Reaction equation

HRID 842748 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][NH2:12].C(N(CC)CC)C>C1COCC1>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][NH:12][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 211563-MethoxybenzylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 1484598HCID 1484598, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (4.170 g, 36.4 mmol) was added to a solution of 3-methoxybenzylamine (5.000 g, 36.4 mmol) and triethylamine (3.946 g, 39.0 mmol) in THF (100 mL) at room temperature. The mixture was stirred for 18 h and the insolubles were removed by filtration. The organic solution was concentrated to a yellow oil which was purified by flash chromatography (6:4 hexanes:EtOAc to 1:1 hexanes:EtOAc) to yield N-(3-methoxy-benzyl)-methanesulfonamide (7.431 g). 1H NMR (400 MHz, CDCl3) δ 7.26 (m, 1H), 6.92-6.82 (m, 3H), 4.62 (m, 1H), 4.28 (d, 2H), 3.80 (s, 3H), 2.87 (s, 3H); MS 214 (M−1).

Workup

  1. customthe insolubles were removed by filtration
  2. concentrationThe organic solution was concentrated to a yellow oil which
  3. customwas purified by flash chromatography (6:4 hexanes:EtOAc to 1:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-fcc2f597a8284217980e062349dbfceb
Source dataset
uspto-grants-2002_04
Patent number
US06376502B1

Reaction notes

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