Pyridine → N-(2-Chloro-4-fluorosulphonylphenyl)-2-acetoxy-2-methylpropanamide

HRID 433331Notes

Reaction equation

HRID 433331 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([S:9]([F:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:13]([O:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19])(=[O:15])[CH3:14].N1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:8]=[C:7]([S:9]([F:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH:4][C:18](=[O:19])[C:17]([O:16][C:13](=[O:15])[CH3:14])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1234962-Acetoxyisobutyroyl chlorideHCID 2827514-Amino-3-chlorobenzenesulfonyl fluoride

Product 1

HCID 18758703N-(2-Chloro-4-fluorosulphonylphenyl)-2-acetoxy-2-methylpropanamideYield 49.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-chloro-4-fluorosulphonylaniline (2.5 g, 12 mmol), 2-acetoxyisobutyryl chloride (2.35 g, 14 mmol) and pyridine (1.2 ml, 14.5 mmol), in DCM (50 ml) was stirred at ambient temperature for 18 h. The mixture was washed with water, dried and evaporated to dryness. The residue was purified by column chromatography using 25% EtOAc/isohexane and the oily product, the title compound (2.0 g, 5.9 mmol), solidified on standing. MS: 336.

Workup

  1. washThe mixture was washed with water
  2. customdried
  3. customevaporated to dryness
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4be0baf51a11426498c953b2f9f7af64
Source dataset
uspto-grants-2003_12
Patent number
US06667342B1

Reaction notes

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