Dimethylformamide → HCID 22419940, compound

HRID 1720034Notes

Reaction equation

HRID 1720034 reaction equation
[S:1]1[C:5]2[C:6]([S:10]([OH:13])(=[O:12])=O)=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.S(Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+].C[N:25]([CH3:28])[CH:26]=O>>[S:1]1[C:5]2[C:6]([S:10]([N:3]3[CH2:4][CH2:5][CH2:28][NH:25][CH2:26][CH2:2]3)(=[O:12])=[O:13])=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 219892071,3-Benzothiazole-7-sulfonic acid

Product 1

HCID 22419940HCID 22419940, compoundYield 65%

Procedure

To 12 g of 7-benzothiazolesulfonic acid were added 120 ml of thionyl chloride and 1.2 ml of dimethylformamide. The resultant mixture was heated under reflux for 3 hours and the thionyl chloride was removed by distillation under reduced pressure to obtain a residue. The thus obtained residue was dissolved in 100 ml of ice water and adjusted to a pH of 6 with a saturated aqueous sodium carbonate solution. The resultant solution is subjected to extraction with 100 ml of dichloromethane, followed by separation of a dichloromethane phase. The dichloromethane phase was dropwise added to 100 ml of a dichloromethane solution containing 16.8 g of homopiperazine over 30 minutes while cooling with ice. The resultant mixture was stirred at a temperature of 0° C. to 5° C. for 1 hour to carry out a reaction. After completion of the reaction, the resultant mixture was washed with 200 ml of water and dried over anhydrous magnesium sulfate. Then, solvent removal was conducted by distillation under reduced pressure to obtain a residue. The thus obtained residue was subjected to purification by means of a chromatography column packed with 600 g of silica gel (Wakogel C-200, manufactured and sold by Wako Pure Chemical Industries, Ltd., Japan), using a mixed solvent of methanol and chloroform (5 to 10% methanol) as an eluent, to thereby obtain 10.8 g of 1-(7-benzothiazolesulfonyl)homopiperazine (yield: 65%).

Workup

  1. temperatureunder reflux for 3 hours
  2. customthe thionyl chloride was removed by distillation under reduced pressure
  3. customto obtain a residue
  4. extractionThe resultant solution is subjected to extraction with 100 ml of dichloromethane
  5. customfollowed by separation of a dichloromethane phase
  6. additionThe dichloromethane phase was dropwise added to 100 ml of a dichloromethane solution
  7. additioncontaining 16.8 g of homopiperazine over 30 minutes
  8. temperaturewhile cooling with ice
  9. customa reaction
  10. customAfter completion of the reaction
  11. washthe resultant mixture was washed with 200 ml of water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customThen, solvent removal
  14. distillationwas conducted by distillation under reduced pressure
  15. customto obtain a residue
  16. customThe thus obtained residue was subjected to purification by means of a chromatography column

Sources & evidence

ORD record
ord-56d69da05ec34e4b993854351deba11b
Source dataset
uspto-grants-1996_04
Patent number
US05504098

Reaction notes

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