Water → HCID 18932236, compound

HRID 1597794Notes

Reaction equation

HRID 1597794 reaction equation
C(N(CC)CC)C.Cl[C:9]([O:11][CH3:12])=[O: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:9](=[O:10])[O:11][CH3:12])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 18932285HCID 18932285, compound

Product 1

HCID 18932236HCID 18932236, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.14 ml of triethylamine and 0.08 ml of methyl chloroformate were added to a solution of 250 mg of 4-(benzothiazol-2-ylmethoxy)aniline [prepared as described in Example 3(b)] in 5 ml of methylene chloride cooled in an ice-water bath and the resulting mixture was stirred at the same temperature for 50 minutes. The temperature of the reaction mixture was then elevated to room temperature and the mixture was stirred for a further 30 minutes. 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 then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure to give a residue which was purified by column chromatography through silica gel using a 3:1 by volume mixture of hexane and ethyl acetate to give 243.1 mg (yield 79%) of the title compound as a solid having a melting point of 142°-144° C.

Workup

  1. temperaturecooled in an ice-water bath
  2. customwas then elevated to room temperature
  3. stirringthe mixture was stirred for a further 30 minutes
  4. extractionthe resulting mixture was extracted with methylene chloride
  5. extractionThe resulting extract
  6. washwashed 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 residue which
  10. customwas purified by column chromatography through silica gel using a 3:1
  11. additionby volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-ddc08f416c9a4f6f98bbca84dc73628b
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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