Hydrochloric Acid → HCID 12017656, compound

HRID 1279593Notes

Reaction equation

HRID 1279593 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1/[CH:9]=[CH: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.Cl>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/[CH:9]=[CH: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 3

HCID 313Hydrochloric AcidHCID 73984-Chlorobenzenesulfonyl chlorideHCID 12017655HCID 12017655, compound

Product 1

HCID 12017656HCID 12017656, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To methyl 4-[2-(2-amino-5-chlorophenyl)-(E)-vinyl]benzoate (130 mg; prepared in Reference Example 5.) in methylene chloride (3 ml), pyridine (0.073 μl) and p-chlorobenzenesulfonylchloride (114 mg) were added. The mixture was stirred overnight at room temperature. The reaction mixture was poured into diluted HCl and extracted with ethyl acetate. The organic layer was washed, dried over and concentrated under the reduced pressure. The residue was purified on silica gel column chromatography (AcOEt-hexane) to give the title compound (205 mg) having the following physical data.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed
  3. customdried over and
  4. concentrationconcentrated under the reduced pressure
  5. customThe residue was purified on silica gel column chromatography (AcOEt-hexane)

Sources & evidence

ORD record
ord-7e8af38d29d2422b9f349074091bfb76
Source dataset
uspto-grants-2002_09
Patent number
US06448290B1

Reaction notes

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