Chloroacetyl chloride → HCID 57966800, compound

HRID 420559Notes

Reaction equation

HRID 420559 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:18]=[CH:17][C:7]2[N:8]=[C:9]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[S:10][C:6]=2[CH:5]=1.C(N(CC)CC)C.C1COCC1.[Cl:31][CH2:32][C:33](Cl)=[O:34]>C(OCC)(=O)C.O>[Cl:31][CH2:32][C:33]([N:14]1[CH2:15][CH2:16][N:11]([C:9]2[S:10][C:6]3[CH:5]=[C:4]([Cl:3])[CH:18]=[CH:17][C:7]=3[N:8]=2)[CH2:12][CH2:13]1)=[O:34]

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66658027HCID 66658027, compound

Product 1

HCID 57966800HCID 57966800, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-(6-chlorobenzothiazole-2-yl)piperazine dihydrochloride (0.50 g; 1.53 mmol), triethylamine (0.32 ml; 2.25 mmol) and anhydrous THF (10 ml) was added dropwise chloroacetylchloride (0.18 ml; 2.25 mmol) under ice-cooling. The mixture was stirred at room temperature for 24 hours. Water and ethyl acetate were added to the reaction solution and extracted. The organic layer was washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The precipitate was washed with hexane to give 2-chloro-1-[4-(6-chlorobenzothiazole-2-yl)piperazine-1-yl]ethane-1-on as blackish brown crystal (0.15 g; 30%).

Workup

  1. temperaturecooling
  2. extractionextracted
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated under reduced pressure
  6. washThe precipitate was washed with hexane

Sources & evidence

ORD record
ord-eb83fe67ae954cfcab6036f82d75b67b
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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