2,5-Dichlorobenzenesulfonyl chloride → 2,4-Dimethyl-1-[3-(2,5-dichlorbenzenesulphonamido)propyl]-pyrrolidine

HRID 1731540Notes

Reaction equation

HRID 1731540 reaction equation
[CH3:1][CH:2]1[CH2:6][CH:5]([CH3:7])[CH2:4][N:3]1[CH2:8][CH2:9][CH2:10][NH2:11].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[S:20](Cl)(=[O:22])=[O:21]>C1C=CC=CC=1>[CH3:1][CH:2]1[CH2:6][CH:5]([CH3:7])[CH2:4][N:3]1[CH2:8][CH2:9][CH2:10][NH:11][S:20]([C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[Cl:12])(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 794012,5-Dichlorobenzenesulfonyl chlorideHCID 202277352,4-Dimethyl-1-(3-aminopropyl)pyrrolidine

Product 1

HCID 202277722,4-Dimethyl-1-[3-(2,5-dichlorbenzenesulphonamido)propyl]-pyrrolidineYield 67%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

2,4-Dimethyl-1-(3-aminopropyl)pyrrolidine in (4.7 g, 0.03 mol) benzene (30 ml) was added dropwise at room temperature to a solution of 2,5-dichlorobenzenesulphonylchloride (7.3 g, 0.03 ml) in benzene (100 ml). Thereafter, the mixture was stirred for 4 days at room temperature until the reaction was complete. Finally, the reaction product was obtained as a viscous, oily paste. The benzene mother liquor was decanted. The residue was dissolved in water, the solution was adjusted to pH 9.8 with 10% NaOH and extractes with petroleum ether (40°-60°) (4×100 ml). The combined extracts were dried over Na2SO4 and evaporated. The residue (5 g) was recrystallised twice from 100 ml petroleum ether to yield the product (3.7 g as white needles), m.p. 65°-67° C. Yield=67% of theoretical

Workup

  1. customFinally, the reaction product was obtained as a viscous, oily paste
  2. customThe benzene mother liquor was decanted
  3. dissolutionThe residue was dissolved in water
  4. customwas adjusted to pH 9.8 with 10% NaOH and extractes with petroleum ether (40°-60°) (4×100 ml)
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. customevaporated
  7. customThe residue (5 g) was recrystallised twice from 100 ml petroleum ether
  8. customto yield the product (3.7 g as white needles), m.p. 65°-67° C

Sources & evidence

ORD record
ord-3e6134f02812472faa64f0e57b1f1f9e
Source dataset
uspto-grants-1986_11
Patent number
US04622331

Reaction notes

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