Water → HCID 18932144, compound

HRID 1597820Notes

Reaction equation

HRID 1597820 reaction equation
[H-].[Na+].[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:24])[O:22][CH3:23])=[C:16]([CH3:25])[CH:15]=1.[Cl:26][CH:27]([CH3:31])[C:28](Cl)=[O:29].O>CN(C)C=O>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]([C:21]([O:22][CH3:23])=[O:24])[C:28](=[O:29])[CH:27]([Cl:26])[CH3:31])=[C:16]([CH3:25])[CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1110192-Chloropropionyl chlorideHCID 18932257methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]carbamate

Product 1

HCID 18932144HCID 18932144, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

18 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 100 mg of methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]carbamate (prepared as described in Example 22 above) in 4 ml of dimethylformamide cooled in an ice-water bath. The resulting mixture was stirred for 15 minutes at the same temperature, after which 0.059 mi of 2-chloropropionyl chloride were added. 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, water 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. The resulting.; residue was purified by preparative thin layer chromatography using a 1:1 by volume mixture of hexane and ethyl acetate to give 70 mg (yield 54%) of the title compound as an oil.

Workup

  1. temperaturecooled 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 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. customresidue was purified by preparative thin layer chromatography
  10. additionby volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-9f11f8f130984ca5b97ec920e105cf9b
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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