Dichloromethane → HCID 15196159, compound

HRID 744100Notes

Reaction equation

HRID 744100 reaction equation
C(Cl)Cl.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([S:16](Cl)(=[O:18])=[O:17])[CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13].C([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=O.C(N(CC)CC)C>O>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([S:16]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)(=[O:18])=[O:17])[CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 821911-PiperazinecarboxaldehydeHCID 151961583,4,5-Trimethoxybenzene-1-sulfonyl chloride

Product 1

HCID 15196159HCID 15196159, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

75 ml of a methylene chloride solution containing 7.40 g of 3,4,5-trimethoxybenzenesulfonyl chloride were dropped into 150 ml of a methylene chloride solution containing 3.80 g of N-formylpiperazine and 7.73 ml of triethylamine in an ice bath. The mixture was then stirred for 30 minutes at 0° to 5° C., after which it was poured into water and extracted twice with methylene chloride. The combined methylene chloride extracts were washed with 10% w/v aqueous hydrochloric acid and with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and condensed by evaporation under reduced pressure. The residue (9.86 g) was dissolved in a mixture of 150 ml of tetrahydrofuran, 75 ml of methanol and 50 ml of a 10% w/v aqueous solution of sodium hydroxide, and then stirred for 14 hours at room temperature. At the end of this time, the reaction solution was poured into water and extracted 4 times with methylene chloride. The combined methylene chloride extracts were washed with water, dried over anhydrous sodium sulfate and condensed by evaporation under reduced pressure. The residue was crystallized from a mixture of hexane and ethyl acetate, to give 7.02 g of the title compound as crylstals, melting at 131° to 133° C.

Workup

  1. extractionextracted twice with methylene chloride
  2. washThe combined methylene chloride extracts were washed with 10% w/v aqueous hydrochloric acid and with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate and condensed by evaporation under reduced pressure
  4. dissolutionThe residue (9.86 g) was dissolved in a mixture of 150 ml of tetrahydrofuran, 75 ml of methanol and 50 ml of a 10% w/v aqueous solution of sodium hydroxide
  5. stirringstirred for 14 hours at room temperature
  6. additionAt the end of this time, the reaction solution was poured into water
  7. extractionextracted 4 times with methylene chloride
  8. washThe combined methylene chloride extracts were washed with water
  9. dry with materialdried over anhydrous sodium sulfate and condensed by evaporation under reduced pressure
  10. customThe residue was crystallized from a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-a045b230de3d497a9751da873a37dc5a
Source dataset
uspto-grants-1996_09
Patent number
US05559109

Reaction notes

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