Water → HCID 851643, compound

HRID 1597774Notes

Reaction equation

HRID 1597774 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:11])[CH2:9][CH3:10].[S:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[CH2:22][O:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1.O>C(Cl)Cl>[S:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[CH2:22][O:23][C:24]1[CH:30]=[CH:29][C:27]([NH:28][C:8](=[O:11])[CH2:9][CH3:10])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 18932285HCID 18932285, compound

Product 1

HCID 851643HCID 851643, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.09 ml of triethylamine and 0.06 ml of propionyl chloride were added to a solution of 149.1 mg of 4-(benzothiazol-2-ylmethoxy)aniline [prepared as described in step (a) above] in 6 ml of methylene chloride cooled in an ice-water bath, and the resulting mixture was stirred at the same temperature for 3 hours. At the end of this time, water was added to the reaction mixture and the resulting mixture was extracted with methylene chloride. The extract was washed with water, dried over anhydrous sodium sulfate and the solvent was then removed under reduced pressure. The resulting residue was purified by column chromatography through silica gel using a 1:2 by volume mixture of hexane and ethyl acetate to give 165.5 mg of the title compound (yield 91%) as a solid having a melting point of 182° C.

Workup

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

Sources & evidence

ORD record
ord-808a46be795841c78689378f5993fc77
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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