Water → HCID 12017670, compound

HRID 1279598Notes

Reaction equation

HRID 1279598 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][O:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.O>C(Cl)Cl.N1C=CC=CC=1>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=2[CH2:9][O:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 962WaterHCID 73984-Chlorobenzenesulfonyl chlorideHCID 12017669HCID 12017669, compound

Product 1

HCID 12017670HCID 12017670, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-(2-amino-5-chlorophenylmethoxy)benzoate (450 mg; prepared in Reference Example 10.) in methylene chloride (4 ml), pyridine (0.24 ml) and 4-chlorobenzenesulfonylchloride (380 mg) were added. The mixture was stirred for 21 hour. To the reaction mixture, water was added. The mixture was extracted with ethyl acetate. The organic layer was washed, dried over and concentrated under the reduced pressure. The residue was purified by recrystallization from hexane-AcOEt mixture solvent to give the title compound (310 mg) having the following physical data.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed
  3. customdried over and
  4. concentrationconcentrated under the reduced pressure
  5. customThe residue was purified by recrystallization from hexane-AcOEt mixture solvent

Sources & evidence

ORD record
ord-2654c58d3c6c447cb7a9fb7e1d58ee51
Source dataset
uspto-grants-2002_09
Patent number
US06448290B1

Reaction notes

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