Benzenesulfonamide → HCID 86688728, compound

HRID 1527954Notes

Reaction equation

HRID 1527954 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[C:6]([CH:17]=1)[CH2:7][N:8]1[C:12]([CH3:13])=[CH:11][C:10]([C:14](F)=[O:15])=[N:9]1.C([O-])([O-])=O.[K+].[K+].[C:34]1([S:40]([NH2:43])(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[C:6]([CH:17]=1)[CH2:7][N:8]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]([NH:43][S:40]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=[O:42])=[O:41])=[O:15])=[N:9]1

Participants

6

Reactant 3

HCID 7370BenzenesulfonamideHCID 11430Potassium CarbonateHCID 86688729HCID 86688729, compound

Product 1

HCID 86688728HCID 86688728, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-[5-chloro-2-(4-methoxy-benzyloxy)-benzyl]-5-methyl-1H-pyrazole-3-carbonyl fluoride, 15, 0.06 g (0.18 mmol) and K2CO3 0.100 g (0.72 mmol) in dry DCM (2 mL), benzenesulfonamide 0.055 g (0.35 mmol) was added. The mixture was stirred under a nitrogen atmosphere for 16 hours before diluting with EtOAc. The organic phase was washed with 2M HCl, followed by brine, dried over MgSO4 and evaporated to dryness. The crude acyl sulphonamide was purified on silica to yield N-{1-[5-chloro-2-(4-methoxy-benzyloxy)-benzyl]-5-methyl-1H-pyrazole-3-carbonyl}-benzenesulfonamide, 16.

Workup

  1. washThe organic phase was washed with 2M HCl
  2. dry with materialdried over MgSO4
  3. customevaporated to dryness
  4. customThe crude acyl sulphonamide was purified on silica

Sources & evidence

ORD record
ord-b8882e5dc11b4436bd54cbabf698a632
Source dataset
uspto-grants-2015_07
Patent number
US09090566B2

Reaction notes

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