Hydrochloric Acid → 4-(Tert-butyl)-n-{3-(2-hydroxyethoxy)-1-methyl-4-[4-(trifluoromethyl)phenyl]-1h-pyrazol-5-yl}benzenesulfonamide

HRID 1368581Notes

Reaction equation

HRID 1368581 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]([C:21]2[N:25]([CH3:26])[N:24]=[C:23]([O:27][CH2:28][CH2:29][OH:30])[C:22]=2[C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=2)COCCOC)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl>C(O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:21]2[N:25]([CH3:26])[N:24]=[C:23]([O:27][CH2:28][CH2:29][OH:30])[C:22]=2[C:31]2[CH:32]=[CH:33][C:34]([C:37]([F:40])([F:38])[F:39])=[CH:35][CH:36]=2)(=[O:12])=[O:13])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 222819664-(tert-butyl)-N-{3-(2-hydroxyethoxy)-1-methyl-4-[4-(trifluoromethyl)phenyl]-1H-pyrazol-5-yl}-N-[(2-methoxyethoxy)methyl]benzenesulfonamide

Product 1

HCID 222819594-(Tert-butyl)-n-{3-(2-hydroxyethoxy)-1-methyl-4-[4-(trifluoromethyl)phenyl]-1h-pyrazol-5-yl}benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 4-(tert-butyl)-N-{3-(2-hydroxyethoxy)-1-methyl-4-[4-(trifluoromethyl)phenyl]-1H-pyrazol-5-yl}-N-[(2-methoxyethoxy)methyl]benzenesulfonamide (Preparation 12) in ethanol (1.5 ml) was added hydrochloric acid (6M, 1.5 ml). The reaction mixture was refluxed for 5 hours and then left at room temperature overnight. The reaction was concentrated under reduced pressure and the residue was partitioned between water (10 ml) and ethyl acetate (10 ml). The aqueous was extracted with ethyl acetate (2×20 ml). The organics were combined, dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield the desired product (120 mg) as a white solid. Taken on crude to the next step.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customthe residue was partitioned between water (10 ml) and ethyl acetate (10 ml)
  4. extractionThe aqueous was extracted with ethyl acetate (2×20 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0463e8a1c79f46d985e5e92f639a0821
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

Loading…