Triethylamine → HCID 70505000, compound

HRID 2295488Notes

Reaction equation

HRID 2295488 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.C([N:15](CC)CC)C.[C:20]1([S:26](Cl)=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]1.[CH:23]1[CH:24]=[CH:25][C:20]([S:26]([NH2:15])=[O:27])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 944591-(2-Pyridyl)piperazineHCID 4190003Benzenesulfinyl chloride

Product 1

HCID 70505000HCID 70505000, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 4.90 g of 1-(2-pyridyl)piperazine in 150 ml of dichloromethane containing 4.59 ml of triethylamine is added dropwise with stirring under nitrogen a solution of 4.82 g of benzenesulfinyl chloride in 50 ml of dichloromethane. The reaction mixture is stirred for 3 hours at room temperature, diluted with 100 ml of dichloromethane, and washed with 150 ml water and 100 ml 5% potassium carbonate. The organic layer is dried over sodium sulfate and evaporated in vacuo to give a yellow crystalline solid. Recrystallization from ethanol affords 4.14 g of 1-(2-pyridyl)piperazine-4-benzenesulfinamide as a colorless crystalline solid, mp 83°-86° (soften 81°). A second crop (1.24 g) is obtained by concentration of the mother liquors, total yield: 5.38 g.

Workup

  1. washwashed with 150 ml water and 100 ml 5% potassium carbonate
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. customevaporated in vacuo
  4. customto give a yellow crystalline solid
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-5e181d8ac2d640989759296c90997302
Source dataset
uspto-grants-1984_01
Patent number
US04425342

Reaction notes

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