Water → HCID 18932301, compound

HRID 1597795Notes

Reaction equation

HRID 1597795 reaction equation
C(N(CC)CC)C.Cl[C:9]([O:11][CH2:12][CH3:13])=[O:10].[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[CH2:23][O:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1.O>C(Cl)Cl>[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[CH2:23][O:24][C:25]1[CH:31]=[CH:30][C:28]([NH:29][C:9](=[O:10])[O:11][CH2:12][CH3:13])=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 18932285HCID 18932285, compound

Product 1

HCID 18932301HCID 18932301, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.14 ml of triethylamine and 0.08 ml of ethyl chloroformate were added to a solution of 250 mg of 4-(benzothiazol-2-ylmethoxy)aniline [prepared as described in Example 3(b) above] in 5 ml of methylene chloride cooled in an ice-water bath, and the resulting mixture was then stirred for 1.5 hours. At the end of this time, water was added to the reaction mixture and the resulting mixture was extracted with methylene chloride. The resulting extract was washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure and the resulting residue was purified by column chromatography through silica gel using a 3:1 by volume mixture of hexane and ethyl acetate to give 284.8 mg (yield 88%) of the title compound as a solid having a melting point of 149°-150° C.

Workup

  1. temperaturecooled in an ice-water bath
  2. extractionthe resulting mixture was extracted with methylene chloride
  3. extractionThe resulting extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was then removed by evaporation under reduced pressure
  7. customthe resulting residue was purified by column chromatography through silica gel using a 3:1
  8. additionby volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-b4d453902e584311944850849bcc4f97
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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