4-Methoxybenzenesulfonyl chloride → N-(4-Chlorophenyl)-4-methoxybenzenesulfonamide

HRID 1503083Notes

Reaction equation

HRID 1503083 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.[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.C(N(CC)CC)C>ClCCl>[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][S:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:11])=[O:10])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 78124-ChloroanilineHCID 8471Triethylamine

Product 1

HCID 598671N-(4-Chlorophenyl)-4-methoxybenzenesulfonamideYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxybenzenesulfonyl chloride (5.0 g, 24 mmol) and 4-chloroaniline (3.1 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 4.9 g (69%) of the product as a tan-colored oil: 1H-NMR (CDC3) δ 10.17 (s, 1H), 7.71 (d, 2H), 7.61 (d, 2H), 7.04 (d, 2H), 6.96 (d, 2H), 2.19 (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-1f054c19907c40dfabb53d9c7b519679
Source dataset
uspto-grants-2015_12
Patent number
US09212134B2

Reaction notes

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