4-Methoxybenzenesulfonyl chloride → HCID 18626203, compound

HRID 1387570Notes

Reaction equation

HRID 1387570 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.[NH2:13][C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:13][C:14]2[CH:15]=[C:16]([CH:26]=[CH:27][C:28]=2[O:29][CH3:30])[C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:18])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 84263-Amino-4-methoxybenzanilide

Product 1

HCID 18626203HCID 18626203, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-methoxybenzenesulfonyl chloride (2.21 g, 10.0 mmol), 3-amino-4-methoxy-N-phenyl-benzamide (2.43 g, 10.0 mmol) and pyridine (25 mL) was allowed to stand at room temperature until thin layer chromatography indicated the reaction to be complete. The mixture was then partitioned between water (400 mL) and ethyl acetate (400 mL). The layers were separated and the organic layer washed with water (2×400 mL), 1N HCL (100 mL), and brine (100 mL) dried (magnesium sulfate), filtered and stripped of solvent. Trituration of the residue in hexanes/ethyl acetate (1:1) and filtration afforded the product (3.754 g); m.p. 184-186° C.

Workup

  1. customto stand at room temperature until thin layer chromatography
  2. customthe reaction
  3. customThe mixture was then partitioned between water (400 mL) and ethyl acetate (400 mL)
  4. customThe layers were separated
  5. washthe organic layer washed with water (2×400 mL), 1N HCL (100 mL), and brine (100 mL)
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. filtrationTrituration of the residue in hexanes/ethyl acetate (1:1) and filtration

Sources & evidence

ORD record
ord-32b35d4127e44678bca40daa53923904
Source dataset
uspto-grants-2001_07
Patent number
US06268387B1

Reaction notes

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