Ethyl chloroformate → HCID 18932354, compound

HRID 1597813Notes

Reaction equation

HRID 1597813 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:23])[CH3:22])=[CH:16][CH:15]=1.Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26].[Cl-].[NH4+]>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:25]([O:27][CH2:28][CH3:29])=[O:26])[C:21](=[O:23])[CH3:22])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 7642407HCID 7642407, compound

Product 1

HCID 18932354HCID 18932354, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

28 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 187 mg of N-[4-(benzothiazol-2-ylmethoxy)phenyl]acetamide (prepared as described in Example 1 above) in 4 ml of dimethylformamide cooled in an ice-water bath. The resulting mixture was stirred for 5 minutes at the same temperature, after which 0.066 ml of ethyl chloroformate were added, the temperature of the resulting mixture was elevated to room temperature and the mixture was stirred for 5 hours. At the end of this time, the reaction mixture was added to a saturated aqueous ammonium chloride solution 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 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 25.6 mg (yield 81%) of the title compound as a solid having a melting point of 155° to 160° C.

Workup

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

Sources & evidence

ORD record
ord-c6c916acb0344c2490ad4bf5afc1c41d
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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