4-Chlorobenzenesulfonyl chloride → HCID 12017677, compound

HRID 1006539Notes

Reaction equation

HRID 1006539 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]#[C: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>C(Cl)Cl.N1C=CC=CC=1.C(OCC)(=O)C>[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[C:9]#[C:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=2)(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

6

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 12017676HCID 12017676, compound

Product 1

HCID 12017677HCID 12017677, compoundYield 94.5%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4-[2-(2-amino-5-chlorophenyl)ethynyl]benzoate (136 mg; prepared in Reference Example 16.) in methylene chloride (2 ml), pyridine (77 μl) and 4-chlorobenzenesulfonyl chloride (106 mg) were added at 0° C. under an atmosphere of argon. The mixture was stirred for 24 hours at room temperature. The reaction mixture was diluted with ethyl acetate, washed, dried over and concentrated under the reduced pressure. The residue was purified on silica gel column chromatography (hexane-AcOEt) to give the title compound (207 mg) having the following physical data.

Workup

  1. washwashed
  2. customdried over and
  3. concentrationconcentrated under the reduced pressure
  4. customThe residue was purified on silica gel column chromatography (hexane-AcOEt)

Sources & evidence

ORD record
ord-e311b5418fd148788c0ec20b252aa74f
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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