Pyridine → N-(2,2-Dimethoxyethyl)-N-[(2-fluorophenyl)methyl]-4-methylbenzenesulfonamide

HRID 1521568Notes

Reaction equation

HRID 1521568 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][CH2:6][CH:7]([O:10][CH3:11])[O:8][CH3:9].N1C=CC=CC=1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>ClCCl>[CH3:11][O:10][CH:7]([O:8][CH3:9])[CH2:6][N:5]([CH2:4][C:3]1[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=1[F:1])[S:28]([C:25]1[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=1)(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 60657374HCID 60657374, compound

Product 1

HCID 89155471N-(2,2-Dimethoxyethyl)-N-[(2-fluorophenyl)methyl]-4-methylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(2-fluorobenzyl)-2,2-dimethoxyethanamine (BB; 33.0 g, 0.154 mol) were dissolved in 200 mL of dichloromethane and pyridine (50.2 g, 0.417 mol) was added. At 0° C. a solution of p-toluene sulphonyl chloride (58.0 g, 0.201 mol) in dichloromethane (500 mL) was added drop wise. The reaction was allowed to warm to room temperature and stirring is continued until conversion was completed. For workup, the reaction mixture was extracted twice with 2M aqueous hydrochloric acid, twice with saturated aqueous sodium bicarbonate and once with saturated aqueous sodium chloride solution. The organic layer was dried over sodium sulphate, evaporated to dryness and the obtained crude product was purified by silica gel chromatography to yield the title compound. 1H NMR (400 MHz, CDCl3) δ 7.69-7.67 (2H, m), 7.43-7.39 (m, 1H), 7.29-7.21 (m, 3H), 7.12-7.08 (m, 1H), 6.99-6.95 (m, 1H), 4.52 (s, 2H), 4.39-4.37 (t, 1H, J=5.2 Hz), 3.26-3.24 (m, 8H), 2.42 (s, 3H).

Workup

  1. extractionFor workup, the reaction mixture was extracted twice with 2M aqueous hydrochloric acid, twice with saturated aqueous sodium bicarbonate and once with saturated aqueous sodium chloride solution
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. customevaporated to dryness
  4. customthe obtained crude product
  5. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-fe5255bcd2224020906ef728ccd3b9af
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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