Hydrochloric Acid → HCID 12017646, compound

HRID 1006523Notes

Reaction equation

HRID 1006523 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:5](=[CH:7][CH:8]=[C:9]([Cl:11])[CH:10]=1)[NH2:6].N1C=CC=CC=1.Cl.[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[C:20]1([S:26]([NH:6][C:5]2[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:4]=2[C:3]([O:2][CH3:1])=[O:12])(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 78878Methyl 2-amino-5-chlorobenzoate

Product 1

HCID 12017646HCID 12017646, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloroanthranilic acid methyl ester (400 mg; prepared in Reference Example 1) and pyridine (0.87 ml) in methylene chloride, benzenesulfonylchloride (0.33 ml) was added at 0° C. The solution 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 reduced pressure. The residue was purified on silica gel column chromatography (hexane-AcOEt) to give the title compound (664 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 reduced pressure
  5. customThe residue was purified on silica gel column chromatography (hexane-AcOEt)

Sources & evidence

ORD record
ord-c14328d617e444afa8c8c0971bfb0432
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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