2-Methoxyaniline → 4-methoxy-N-(2-methoxyphenyl)benzenesulfonamide

HRID 1503084Notes

Reaction equation

HRID 1503084 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH3:13][O:14][C:15]1[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=1[NH2:17].C(N(CC)CC)C>ClCCl>[CH3:13][O:14][C:15]1[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=1[NH:17][S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 70002-MethoxyanilineHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 7434174-methoxy-N-(2-methoxyphenyl)benzenesulfonamideYield 75.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxybenzenesulfonyl chloride (5.0 g, 24 mmol) and 2-methoxyaniline (3.0 g, 24 mmol) in dichloromethane (24 mL) at 0° C. was added triethylamine (3.4 mL, 24 mmol) over 10 minutes. The ice bath was removed, and the mixture was stirred for 16 hr. The mixture was diluted with dichloromethane (100 mL) and the combined solution was washed with water (50 mL) and brine (50 mL). The organic solution was dried over MgSO4, filtered, and evaporated, and the crude product was purified by silica gel chromatography (15-60% EtOAc/Hex). Product-containing fractions were pooled, evaporated, and dried under high vacuum to yield 5.3 g (44%) of the product as a tan-colored oil: 1H-NMR (CDCl3) δ 7.70-7.67 (d, 2H), 7.53-7.50 (d, 1H), 7.05-6.99 (m, 2H), 6.91-6.83 (m, 3H), 6.73 (d, 1H), 3.80 (s, 3H), 3.65 (s, 3H).

Workup

  1. customThe ice bath was removed
  2. additionThe mixture was diluted with dichloromethane (100 mL)
  3. washthe combined solution was washed with water (50 mL) and brine (50 mL)
  4. dry with materialThe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customthe crude product was purified by silica gel chromatography (15-60% EtOAc/Hex)
  8. customevaporated
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-27558dc9d9c345b6819f96b64c294c61
Source dataset
uspto-grants-2015_12
Patent number
US09212134B2

Reaction notes

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