4-Methoxybenzenesulfonyl chloride → N-(3-Acetyl-2-hydroxyphenyl)-4-methoxybenzenesulfonamide

HRID 1603924Notes

Reaction equation

HRID 1603924 reaction equation
Br.[NH2:2][C:3]1[C:4]([OH:12])=[C:5]([C:9](=[O:11])[CH3:10])[CH:6]=[CH:7][CH:8]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[C:9]([C:5]1[C:4]([OH:12])=[C:3]([NH:2][S:21]([C:18]2[CH:17]=[CH:16][C:15]([O:14][CH3:13])=[CH:20][CH:19]=2)(=[O:23])=[O:22])[CH:8]=[CH:7][CH:6]=1)(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 196063433'-Amino-2'-hydroxyacetophenone hydrobromide

Product 1

HCID 19606314N-(3-Acetyl-2-hydroxyphenyl)-4-methoxybenzenesulfonamideYield 83.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 3'-amino-2'-hydroxyacetophenone hydrobromide (1.282 g, 5.52 mmol) in pyridine (25 ml) was added at 0° C. with 4-methoxybenzenesulfonyl chloride (1.18 g, 5.71 mmol) dissolved in the minimum amount of pyridine and the mixture was left at room temperature for 18 h. Afterwards it was evaporated to dryness, redissolved in dichloromethane, washed with 1M HCl, dried and the solvent was evaporated off under reduced pressure, thereby obtaining 1.479 g of the title compound (81% yield).

Workup

  1. customAfterwards it was evaporated to dryness
  2. dissolutionredissolved in dichloromethane
  3. washwashed with 1M HCl
  4. customdried
  5. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-4776d61a27c64099be849b27e61d28a8
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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