Dichloromethane → HCID 15290079, compound

HRID 1757527Notes

Reaction equation

HRID 1757527 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:16]=[C:17]([O:21]C)[C:18]=1[O:19]C)[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]([SH:15])=[S:14])[CH2:9][CH2:8]1.C(Cl)Cl.B(Br)(Br)Br>O>[OH:21][C:17]1[CH:16]=[C:5]([CH:4]=[C:3]([OH:2])[C:18]=1[OH:19])[CH2:6][N:7]1[CH2:8][CH2:9][N:10]([C:13]([SH:15])=[S:14])[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 25134Boron tribromideHCID 15290074HCID 15290074, compound

Product 1

HCID 15290079HCID 15290079, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

In a nitrogen atmosphere, 1,033 mg (3.02 mmol.) of 4-(3,4,5-trimethoxybenzyl)-1-piperazinecarbodithioic acid was suspended indry methylene chloride, and under chilling to -78° C. in a dry ice-acetone bath, to this was dropwise added 50 ml of methylene chloride solution containing 3 ml of boron tribromide. The mixture was left to slowly reach room temperature, and then stirred for 5 days at room temperatuere. To the reaction mixture was added water, and insolubles wereremoved by filtration. The insolubles were then washed with water, and thusobtained yellow solid was dissolved in methanol. The methanol solution was filtered to remove insoubles, and the solvent of the filtrate was distilled off. To the obtained yellow semi-oil was added ether, and insolubles were removed by filtration. The filtrate was dried and further purified by cellulose column chromatography (Avicel, trademark, eluent: butanol/acetic acid/water (10/1/1)). The eluate was treated to distill offthe solvent (eluent). To the residue was added ether, and insolubles were removed by filtration. The solvent of the filtrate was distilled off, leaving 103 mg of the desired compound, m.p. higher than 250° C., yield 11.4%.

Workup

  1. waitThe mixture was left to slowly reach room temperature
  2. filtrationwereremoved by filtration
  3. washThe insolubles were then washed with water
  4. dissolutionwas dissolved in methanol
  5. filtrationThe methanol solution was filtered
  6. customto remove insoubles
  7. distillationthe solvent of the filtrate was distilled off
  8. additionTo the obtained yellow semi-oil was added ether, and insolubles
  9. customwere removed by filtration
  10. customThe filtrate was dried
  11. customfurther purified by cellulose column chromatography (Avicel, trademark, eluent: butanol/acetic acid/water (10/1/1))
  12. additionThe eluate was treated
  13. distillationto distill offthe solvent (eluent)
  14. additionTo the residue was added ether, and insolubles
  15. customwere removed by filtration
  16. distillationThe solvent of the filtrate was distilled off

Sources & evidence

ORD record
ord-f489eb6c75924cca996dee33b9e32a45
Source dataset
uspto-grants-1995_08
Patent number
US05446146

Reaction notes

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