Hydrochloric Acid → HCID 12017682, compound

HRID 1006540Notes

Reaction equation

HRID 1006540 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.O.Cl.[CH:32](I)([CH3:34])[CH3:33]>CN(C=O)C.C(=O)([O-])[O-].[K+].[K+]>[CH:32]([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)([CH3:34])[CH3:33]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6362Isopropyl iodideHCID 12017662HCID 12017662, compound

Product 1

HCID 12017682HCID 12017682, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 4-(2-phenylsulfonylamino-4-chlorophenoxy-methyl)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-7de6b4b10eb9462ca2e181c27d372071
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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