Chloroacetyl chloride → HCID 18932280, compound

HRID 1597777Notes

Reaction equation

HRID 1597777 reaction equation
C(N(CC)CC)C.[Cl:8][CH2:9][C:10](Cl)=[O:11].[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.[Cl-].[NH4+]>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:10](=[O:11])[CH2:9][Cl:8])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 18932285HCID 18932285, compound

Product 1

HCID 18932280HCID 18932280, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.24 ml of triethylamine and 0.17 ml of chloroacetyl chloride were added to a solution of 300 mg of 4-(benzothiazol-2-ylmethoxy)aniline [prepared as described in step (b) above] in 6 ml of methylene chloride cooled in an ice-water bath, and the resulting mixture was stirred for 1 hour. After this time, a saturated aqueous ammonium chloride solution was added to the reaction mixture and the resulting mixture was extracted with methylene chloride. The resulting extract was washed with water, dried over anhydrous sodium sulfate and the solvent was then removed by evaporation under reduced pressure. The resulting residue was recrystallized from a mixed solvent of methylene chloride and hexane to obtain 259.4 mg (yield 65.5%) of the title compound as a solid having a melting point of 196° to 197° 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 recrystallized from a mixed solvent of methylene chloride and hexane

Sources & evidence

ORD record
ord-f387b52b339a480186f55ca4e273511a
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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