Benzenesulfonyl chloride, 3,4-dichloro- → HCID 64979891, compound

HRID 1868021Notes

Reaction equation

HRID 1868021 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:13][CH:14]1[CH2:19][NH:18][CH:17]([CH3:20])[CH2:16][NH:15]1.C(N(C(C)C)CC)(C)C>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:15]2[CH2:16][CH:17]([CH3:20])[NH:18][CH2:19][CH:14]2[CH3:13])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 78162,5-DimethylpiperazineHCID 81531Diisopropylethylamine

Product 1

HCID 64979891HCID 64979891, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3,4-dichlorobenzene-1-sulfonyl chloride (840 mg, 3.42 mmol) and 2,5-dimethylpiperazine (1.171 g, 10.26 mmol) in anhydrous dichloromethane (5 mL) was added diisopropylethylamine (1.2 mL, 6.84 mmol). The mixture was stirred overnight at room temperature. Reaction was complete as determined by TLC. The reaction mixture was diluted with dichloromethane, washed with water and dried over MgSO4. After solvent evaporation crude product was treated with ethyl acetate/hexanes. Solid impurity was filtered of and the filtrate was concentrated to afford 1-(3,4-dichlorophenylsulfonyl)-2,5-dimethylpiperazine in quantitative yield. It was carried to the next step without further purification.

Workup

  1. customReaction
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. customAfter solvent evaporation crude product
  5. additionwas treated with ethyl acetate/hexanes
  6. filtrationSolid impurity was filtered of and the filtrate
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-76ff9e2c1cee46b9a3b269054c221fe1
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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