3,5-Dichlorobenzenesulfonyl chloride → HCID 18626128, compound

HRID 1859724Notes

Reaction equation

HRID 1859724 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([F:15])[CH:9]=1)=[O:6].[Cl:21][C:22]1[CH:23]=[C:24]([S:29](Cl)(=[O:31])=[O:30])[CH:25]=[C:26]([Cl:28])[CH:27]=1>N1C=CC=CC=1>[Cl:28][C:26]1[CH:25]=[C:24]([S:29]([NH:1][C:2]2[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=2[O:19][CH3:20])[C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([F:15])[CH:9]=2)=[O:6])(=[O:30])=[O:31])[CH:23]=[C:22]([Cl:21])[CH:27]=1

Participants

4

Reactant 2

HCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 10755041HCID 10755041, compound

Product 1

HCID 18626128HCID 18626128, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-amino-4-methoxy-N-(3,4-difluorophenyl)-benzamide from Example 15 (0.834 g, 3.00 mmol), 3,5-dichlorobenzenesulfonyl chloride (0.736 g, 3.00 mmol) and a catalytic amount of 4-dimethylaaminopyridine in pyridine (10 mL) was stirred under nitrogen at room temperature. After 16 hours, the solvent was removed in vacuo and the residue shaken with a mixture of ethyl acetate and 1N HCl then filtered. The layers were separated and the organic layer washed with brine, dried with MgSO4, concentrated to dryness, triturated in hexanes and filtered to afford a solid which was combined with that obtained in the filtration step to afford the product (1.38 g); m.p. 228-231° C.

Workup

  1. customthe solvent was removed in vacuo
  2. filtrationthen filtered
  3. customThe layers were separated
  4. washthe organic layer washed with brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated to dryness
  7. customtriturated in hexanes
  8. filtrationfiltered
  9. customto afford a solid which
  10. customthat obtained in the filtration step

Sources & evidence

ORD record
ord-69937c81888947708fdc3ba93482a5a0
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

Loading…