1-Chloro-4-nitrobenzene → HCID 70123326, compound

HRID 1597788Notes

Reaction equation

HRID 1597788 reaction equation
CC(C)([O-])C.[K+].Cl[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.[OH:17][C:18]([C:21]1[S:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1)([CH3:20])[CH3:19].[Cl-].[NH4+]>CN(C)C=O>[S:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=[C:21]1[C:18]([O:17][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 74741-Chloro-4-nitrobenzeneHCID 25517Ammonium ChlorideHCID 12399390HCID 12399390, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 70123326HCID 70123326, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

108.9 mg of potassium t-butoxide and 134.1 mg of 4-chloronitrobenzene were added to a solution of 156.6 mg of 2-(1-hydroxy-1-methylethyl)benzothiazole [prepared as described in step (a) above] in 3.1 ml of dimethylformamide at room temperature. The resulting mixture was stirred at room temperature for 3 hours, and then it was stirred at 60° C. for a further 4 hours. The temperature of the reaction mixture was then raised to 90° C. and the mixture stirred at this temperature for a further 5 hours, after which it was cooled to room temperature. A saturated aqueous ammonium chloride solution was then added to the reaction mixture and the mixture was extracted with ethyl acetate. The resulting extract was washed consecutively with water and a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure and the resulting residue was purified by column chromatography through silica gel using a 10:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 197.1 mg (yield 70%) of the title compound as an oil.

Workup

  1. stirringit was stirred at 60° C. for a further 4 hours
  2. temperatureThe temperature of the reaction mixture was then raised to 90° C.
  3. stirringthe mixture stirred at this temperature for a further 5 hours
  4. temperatureafter which it was cooled to room temperature
  5. extractionthe mixture was extracted with ethyl acetate
  6. extractionThe resulting extract
  7. washwas washed consecutively with water
  8. dry with materiala saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate
  9. customThe solvent was then removed by evaporation under reduced pressure
  10. customthe resulting residue was purified by column chromatography through silica gel using a 10:1
  11. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-3e2230a246724780a5cbeddecb505c1b
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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