2-Chlorobenzoic Acid → HCID 14051183, compound

HRID 1199710Notes

Reaction equation

HRID 1199710 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)/[CH:5]=[CH:6]/[C:7]1[S:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1.Cl[C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([OH:24])=[O:23].C(=O)([O-])[O-].[K+].[K+]>[Cu].II.C(O)CC(C)C>[C:22]([C:21]1[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=1[NH:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)/[CH:5]=[CH:6]/[C:7]1[S:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1)([OH:24])=[O:23]

Participants

7

Reactant 3

HCID 83742-Chlorobenzoic AcidHCID 11430Potassium CarbonateHCID 14051212HCID 14051212, compound

Product 1

HCID 14051183HCID 14051183, compoundYield 11.2%

Reagents, catalysts & solvents 3

HCID 807IodineCatalystHCID 23978CopperCatalystHCID 31260Isoamyl AlcoholSolvent

Procedure

To 10 ml of isoamyl alcohol were added 504 mg of 2-(trans-3-aminostyryl)benzothiazole, 311 mg of 2-chlorobenzoic acid, 290 mg of potassium carbonate, 1 mg of iodine and 15 mg of copper powder, and the mixture was refluxed for 6 hours. The solvent was evaporated under reduced pressure and the residue was extracted with ethyl acetate. The crude product after evaporation of the solvent was purified through silica gel column chromatography by use of ethyl acetate-toluene to obtain 83 mg (yield 11%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. customThe solvent was evaporated under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate
  4. customThe crude product after evaporation of the solvent
  5. customwas purified through silica gel column chromatography by use of ethyl acetate-toluene

Sources & evidence

ORD record
ord-c727bc7dcd9d4e3182e4ba20240a1920
Source dataset
uspto-grants-1990_02
Patent number
US04902700

Reaction notes

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