Water → HCID 15290079, compound

HRID 1460163Notes

Reaction equation

HRID 1460163 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.B(Br)(Br)Br.O>C(Cl)Cl>[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 962WaterHCID 25134Boron tribromideHCID 15290074HCID 15290074, compound

Product 1

HCID 15290079HCID 15290079, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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 in dry 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 temperature. To the reaction mixture was added water, and insolubles were removed by filtration. The insolubles were then washed with water, and thus obtained yellow solid was dissolved in methanol. The methanol solution was filtered to remove insolubles, 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 off the 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. customwere removed by filtration
  3. washThe insolubles were then washed with water, and thus obtained yellow solid
  4. dissolutionwas dissolved in methanol
  5. filtrationThe methanol solution was filtered
  6. customto remove insolubles
  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 off the 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-ae80706027a449ee80bb3cbf5f3569dc
Source dataset
uspto-grants-1991_12
Patent number
US05070089

Reaction notes

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