Chloroacetyl chloride → HCID 131716539, compound

HRID 1463469Notes

Reaction equation

HRID 1463469 reaction equation
Cl[CH2:2][C:3](Cl)=[O:4].[C:6]1([C:12]2[S:13][C:14]3[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]=3[N:21]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CN1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.[CH2:29]1COC[CH2:30]1>C(N(CC)CC)C.C(Cl)Cl>[CH3:29][CH:30]1[CH2:28][CH2:27][N:26]([CH2:2][C:3]([N:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C:20]3[N:21]=[C:12]([C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=4)[S:13][C:14]2=3)=[O:4])[CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 531671-MethylpiperazineHCID 9991469HCID 9991469, compound

Product 1

HCID 131716539HCID 131716539, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent2×

Procedure

Chloroacetyl chloride (2.2 g) was added dropwise to a mixture of 2-phenyl-5,6,7,8-tetrahydro-4H-thiazolo[5,4-b]-azepine (3.0 g), triethylamine (3.6 ml) and methylenechloride (100 ml) under ice-cooling and stirring. After stirring for 30 mins. at room temperature, the mixture was distilled under reduced pressure to remove the solvent, and the residue was extracted with chloroform. The extract was washed with a saturated sodium hydrogen carbonate solution, water, dried over anhydrous sodium sulfate and the solvent removed by distillation under reduced pressure to give a crude product (4.0 g). To a solution of the above product (1.9 g) and triethylamine (2.6 ml) in 20 ml of THF was added N-methylpiperazine (1.4 ml), and the whole was stirred for 5 hrs. at room temperature. The reaction mixture was concentrated and extracted with ethyl ether. The extract was washed with water, dried and concentrated under reduced pressure. The residue was purified by a column chromatography on silica gel, converted into a salt of hydrochloric acid and then recrystallized from a mixture of isopropanol and ethyl ether to give the title compound (1.66 g, 56%).

Workup

  1. temperaturecooling
  2. stirringAfter stirring for 30 mins
  3. distillationat room temperature, the mixture was distilled under reduced pressure
  4. customto remove the solvent
  5. extractionthe residue was extracted with chloroform
  6. washThe extract was washed with a saturated sodium hydrogen carbonate solution, water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent removed by distillation under reduced pressure
  9. customto give a crude product (4.0 g)
  10. stirringthe whole was stirred for 5 hrs
  11. customat room temperature
  12. concentrationThe reaction mixture was concentrated
  13. extractionextracted with ethyl ether
  14. washThe extract was washed with water
  15. customdried
  16. concentrationconcentrated under reduced pressure
  17. customThe residue was purified by a column chromatography on silica gel
  18. customrecrystallized from a mixture of isopropanol and ethyl ether

Sources & evidence

ORD record
ord-51d40763ea664c50877cfe9368157e9c
Source dataset
uspto-grants-1994_04
Patent number
US05300639

Reaction notes

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