4-Nitrobenzenesulfonyl chloride → HCID 8194946, compound

HRID 237020Notes

Reaction equation

HRID 237020 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:14]1([CH3:26])[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(N(CC)CC)C>O1CCCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:23]2[CH2:24][CH2:25][N:20]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH3:26])[CH2:21][CH2:22]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 919652-Mepp

Product 1

HCID 8194946HCID 8194946, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7.88 g (0.0356 m) of p-nitrobenzenesulfonylchloride, 6.27 g (0.0356 m) of 1-(o-tolyl)piperazine, 4.96 ml (0.0356 m) of triethylamine, and 100 ml of tetrahydrofuran is stirred at room temperature for 18 hours. The solvent is then removed in vacuo and the residue is extracted with methylene chloride/aqueous sodium bicarbonate and brine. The organic layer is filtered through sodium sulfate and taken to dryness. Crystallization from methylene chloride/Skellysolve® B hexanes gives 9.51 g of 1-[(p-nitrophenyl)sulfonyl]-4-(o-methylphenyl)piperazine of melting point 176°-177.5° C. and 1.33 g of a second crop (84%).

Workup

  1. customThe solvent is then removed in vacuo
  2. extractionthe residue is extracted with methylene chloride/aqueous sodium bicarbonate and brine
  3. filtrationThe organic layer is filtered through sodium sulfate
  4. customCrystallization from methylene chloride/Skellysolve® B hexanes

Sources & evidence

ORD record
ord-68620448e76d48e1af60d0f3ad72d1a5
Source dataset
uspto-grants-1979_06
Patent number
US04159331

Reaction notes

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