Hydrochloric Acid → HCID 12017682, compound

HRID 1279605Notes

Reaction equation

HRID 1279605 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:12]=2[O:13][CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH:36](I)([CH3:38])[CH3:37].Cl>CN(C=O)C.O>[CH:36]([N:10]([S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:8])=[O:9])[C:11]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:12]=1[O:13][CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1)([CH3:38])[CH3:37]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 12017662HCID 12017662, compound

Product 1

HCID 12017682HCID 12017682, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 4-(2-phenylsulfonylamino-4-chlorophenoxymethyl)benzoate (402 mg; prepared in Example 7(a).) in DMF (4 ml), potassium carbonate (256 mg) and isopropyl iodide (185 μl) were added. The mixture was stirred overnight at room temperature and for 9 hours at 50° C. To the reaction solution, iced water and 2N HCl were added. The mixture was extracted with ethyl acetate. The organic layer was washed, dried over, concentrated after filtration, solidified with ethanol and washed to give the title compound (411 mg) having the following physical data.

Workup

  1. additionwere added
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed
  4. customdried over,
  5. concentrationconcentrated
  6. filtrationafter filtration
  7. washwashed

Sources & evidence

ORD record
ord-9c95ee68efe94f57af9226bdc47f8482
Source dataset
uspto-grants-2002_09
Patent number
US06448290B1

Reaction notes

Loading…