Sodium hydride → Methyl N-[4-(benzothiazol-2-ylmethylthio)phenyl]carbamate

HRID 1597812Notes

Reaction equation

HRID 1597812 reaction equation
[H-].[Na+].[SH:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:14])[O:12][CH3:13])=[CH:6][CH:5]=1.Br[CH2:16][C:17]1[S:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1.[Cl-].[NH4+]>CN(C)C=O>[S:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[CH2:16][S:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:14])[O:12][CH3:13])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 603048Carbamic acid, (4-mercaptophenyl)-, methyl esterHCID 27762582-(Bromomethyl)-1,3-benzothiazole

Product 1

HCID 18932163Methyl N-[4-(benzothiazol-2-ylmethylthio)phenyl]carbamateYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100.5 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 418.5 mg of methyl N-(4-mercaptophenyl)carbamate [prepared as described in step (a) above] in 8.4 ml of dimethylformamide cooled in an ice-water bath. The resulting mixture was stirred at the same temperature for 10 minutes, and then 573.1 mg of 2-bromomethylbenzothiazole were added. The temperature of the reaction mixture was then elevated to room temperature and the mixture was stirred for 3.5 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 then removed by evaporation under reduced pressure to give a crude crystalline solid which was purified by column chromatography through silica gel using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 462.7 mg (yield 81%) of the title compound as a solid having a melting point of 139° to 141° C.

Workup

  1. temperaturecooled in an ice-water bath
  2. customwas then elevated to room temperature
  3. stirringthe mixture was stirred for 3.5 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 then 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 4:1
  11. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-6b5e54c02c0b4ea3acf0f6d70c3ba92a
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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