Water → HCID 18932372, compound

HRID 1597775Notes

Reaction equation

HRID 1597775 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([O-:5])=[O:4].Br[CH2:14][C:15]1[S:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1.O>CN(C)C=O>[S:16]1[C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=[C:15]1[CH2:14][C:10]1[CH:11]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=[CH:8][C:9]=1[OH:12]

Participants

6

Reactant 4

HCID 962WaterHCID 9804-NitrophenolHCID 24758Sodium hydrideHCID 27762582-(Bromomethyl)-1,3-benzothiazole

Product 1

HCID 18932372HCID 18932372, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

855.5 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 2.83 g of 4-nitrophenol in 30 ml of dimethylformamide cooled in an ice-water bath. The resulting mixture was stirred at the same temperature for 5 minutes, after which a solution of 4.88 g of 2-bromomethylbenzothiazole in 25 ml of dimethylformamide was added thereto. The temperature of the resulting mixture was elevated to room temperature, and the mixture was then stirred at this temperature for 4 hours. At the end of this time the reaction mixture was cooled in an ice-water bath and 100 ml of water was added to said reaction mixture resulting in the precipitation of a crystalline solid which was filtered off, washed with water and then further washed with hexane. The resulting crude crystalline solid was purified by column chromatography through silica gel using a 10:1 by volume mixture of hexane and ethyl acetate, to give 4.99 g (yield 86%) of the title compound having a melting point of 189° to 191° C.

Workup

  1. temperaturecooled in an ice-water bath
  2. customwas elevated to room temperature
  3. stirringthe mixture was then stirred at this temperature for 4 hours
  4. temperatureAt the end of this time the reaction mixture was cooled in an ice-water bath
  5. customreaction mixture
  6. customresulting in the precipitation of a crystalline solid which
  7. filtrationwas filtered off
  8. washwashed with water
  9. washfurther washed with hexane
  10. customThe resulting crude crystalline solid was purified by column chromatography through silica gel using a 10:1
  11. additionby volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-b0f5cd21575d4c0fbad33b31f6f37e96
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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