Sodium hydride → HCID 18932455, compound

HRID 1597802Notes

Reaction equation

HRID 1597802 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([NH:11][C:12](=[O:15])[O:13][CH3:14])[CH:7]=[CH:8][C:9]=1[OH:10].Br[CH2:17][C:18]1[S:19][C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=1.[Cl-].[NH4+]>CN(C)C=O>[S:19]1[C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=[C:18]1[CH2:17][O:10][C:9]1[CH:8]=[CH:7][C:6]([NH:11][C:12](=[O:15])[O:13][CH3:14])=[CH:5][C:4]=1[Cl:3]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27762582-(Bromomethyl)-1,3-benzothiazoleHCID 18932212Methyl (3-chloro-4-hydroxyphenyl)carbamate

Product 1

HCID 18932455HCID 18932455, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

44.4 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 203.6 mg of methyl N-(3-chloro-4-hydroxyphenyl)carbamate [prepared as described in step (a) above] in 4 ml of dimethylformamide cooled in an ice-water bath. The resulting mixture was stirred at the same temperature for 3 minutes, and then 241.9 mg of 2-bromomethylbenzothiazole were added. The temperature of the reaction mixture was then elevated to room temperature and the mixture was stirred for 1.5 hours. At the end of this time, a saturated aqueous ammonium chloride solution was added to the reaction mixture and the resulting 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 removed by evaporation under reduced pressure to give a crude crystalline solid which was purified by column chromatography through silica gel using a 2:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 286.9 mg (yield 81%) of the title compound as a solid having a melting point of 133°-135° C.

Workup

  1. temperaturecooled in an ice-water bath
  2. customwas then elevated to room temperature
  3. stirringthe mixture was stirred for 1.5 hours
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. extractionThe resulting extract
  6. washwas washed consecutively with water
  7. dry with materiala saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate
  8. customThe solvent was removed by evaporation under reduced pressure
  9. customto give a crude crystalline solid which
  10. customwas purified by column chromatography through silica gel using a 2:1
  11. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-8ec875662a914eef9a30d70b9155f16e
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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