Potassium Carbonate → HCID 58930424, compound

HRID 852928Notes

Reaction equation

HRID 852928 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[NH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].[H-].[Na+]>CN(C=O)C>[CH3:21][O:20][C:18](=[O:19])[C:17]1[CH:22]=[CH:23][C:14]([NH:13][C:2]2[S:3][C:4]3[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12082Methyl 4-aminobenzoateHCID 24758Sodium hydrideHCID 2731322-Chloro-6-methoxybenzothiazole

Product 1

HCID 58930424HCID 58930424, compoundYield 9.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-chloro-6-methoxybenzothiazole (1.00 g, 5.03 mmol) in DMF (10 mL) was added methyl 4-aminobenzoate (760 mg, 5.03 mmol) followed by addition of powdered K2CO3 (1.81 g, 15.09 mmol). The mixture was stirred at 90° C. for 16 h and at 120° C. for 24 h and then at 140° C. for 3 days. It was allowed to cool down to rt and NaH (60% in mineral oil, 201 mg, 5.03 mmol) was added. The mixture was stirred at rt for 16 h and quenched with H2O. The solvent was removed in vacuo at 80° C. and the residue was partitioned between H2O and EtOAc. The organic layer was washed with HCl 1N, saturated NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography using EtOAc/Hex and increasing polarity from 20:80 to 50:50 throughout elution, affording the title compound 161 (150 mg, 9% yield). m/z: 315.2 (MH+)

Workup

  1. waitat 140° C. for 3 days
  2. temperatureto cool down to rt
  3. stirringThe mixture was stirred at rt for 16 h
  4. customquenched with H2O
  5. customThe solvent was removed in vacuo at 80° C.
  6. customthe residue was partitioned between H2O and EtOAc
  7. washThe organic layer was washed with HCl 1N, saturated NaHCO3 and brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe crude material was purified by flash chromatography
  11. temperatureincreasing polarity from 20:80 to 50:50
  12. washthroughout elution

Sources & evidence

ORD record
ord-2318ef051fc44ef8bbc11ae2181e6fe6
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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