Water → HCID 54527691, compound

HRID 1757540Notes

Reaction equation

HRID 1757540 reaction equation
C[O:2][C:3]1[C:8]([O:9]C)=[C:7]([O:11]C)[CH:6]=[CH:5][C:4]=1[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([C:21]([S:23][CH3:24])=[S:22])[CH2:17][CH2:16]1.O.C(=O)([O-])O.[Na+]>ClCCl.B(Br)(Br)Br>[OH:2][C:3]1[C:8]([OH:9])=[C:7]([OH:11])[CH:6]=[CH:5][C:4]=1[CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][N:18]([C:21]([S:23][CH3:24])=[S:22])[CH2:19][CH2:20]1

Participants

6

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 54054438HCID 54054438, compound

Product 1

HCID 54527691HCID 54527691, compoundYield 31.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25134Boron tribromideSolvent2×

Procedure

In 14 ml of dry dichloromethane was dissolved 1 ml of boron tribromide 9.3 ml of the resulting solution containing 665 mmol. of boron tribromide was chilled to -50° C. in a nitrogen atmosphere. To the chilled solution was dropwise added a solution of 0.73 g of methyl 4-{2-(2,3,4-trimethoxyphenyl)ethyl}-1-piperazinecarbodithioate in 25 ml ofdry dichloromethane for 15 min. The resulting mixture was left to reach room temperature, and then stirred overnight. To the mixture was added 3 ml of water, and further added a saturated aqueous sodium hydrogen carbonate solution until the mixture had pH 8. The mixture was then extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and placed under reduced pressure to distill off the solvent, yielding 205 mg of the desired compound as a grayish powder, m.p. 156°-158° C. (decomp.), yield 31.5%.

Workup

  1. additioncontaining 665 mmol
  2. waitThe resulting mixture was left
  3. customto reach room temperature
  4. extractionThe mixture was then extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. distillationto distill off the solvent

Sources & evidence

ORD record
ord-5b1661c86fac4ed78caab46a43d33e24
Source dataset
uspto-grants-1995_08
Patent number
US05446146

Reaction notes

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