Sodium hydride → Methyl N-[4-(6-fluorobenzothiazol-2-ylmethoxy)-2-methylphenyl]carbamate

HRID 1597799Notes

Reaction equation

HRID 1597799 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:14])[O:12][CH3:13])=[C:6]([CH3:15])[CH:5]=1.[F:16][C:17]1[CH:31]=[CH:30][C:20]2[N:21]=[C:22]([CH2:24]OS(C)(=O)=O)[S:23][C:19]=2[CH:18]=1.[Cl-].[NH4+]>CN(C)C=O>[F:16][C:17]1[CH:31]=[CH:30][C:20]2[N:21]=[C:22]([CH2:24][O:3][C:4]3[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:14])[O:12][CH3:13])=[C:6]([CH3:15])[CH:5]=3)[S:23][C:19]=2[CH:18]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 189321066-Fluoro-2-methanesulfonyloxymethylbenzothiazoleHCID 18932138methyl N-(4-hydroxy-2-methylphenyl)carbamate

Product 1

HCID 18932186Methyl N-[4-(6-fluorobenzothiazol-2-ylmethoxy)-2-methylphenyl]carbamateYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15.2 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 62.6 mg of methyl N-(4-hydroxy-2-methylphenyl)carbamate [prepared as described in step (a) above] in 4 ml of dimethylformamide with cooling in an ice-water bath. The resulting mixture was stirred at the same temperature for 10 minutes, and then 100.0 mg of 6-fluoro-2-methanesulfonyloxymethylbenzothiazole [prepared as described in Example 5(c)] were added to the reaction mixture. The temperature of the resulting mixture was elevated to room temperature and the mixture was stirred for 3 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 with water and then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure to give a crude crystalline product which was purified by column chromatography through silica gel using a 3:1 by volume mixture of hexane and ethyl acetate as the eluent, to give a crystalline solid which was washed with diethyl ether and then dried in vacuo to give 41.4 mg (yield 35%) of the title compound as a solid having a melting point of 149°-151° C.

Workup

  1. temperaturewith cooling in an ice-water bath
  2. customwas elevated to room temperature
  3. stirringthe mixture was stirred for 3 hours
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. extractionThe resulting extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was then removed by evaporation under reduced pressure
  9. customto give a crude crystalline product which
  10. customwas purified by column chromatography through silica gel using a 3:1
  11. additionby volume mixture of hexane and ethyl acetate as the eluent
  12. customto give a crystalline solid which
  13. washwas washed with diethyl ether
  14. customdried in vacuo

Sources & evidence

ORD record
ord-5f6e9528c5da47d9bb7d87c49d51c1fc
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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