Triethylamine → HCID 71436066, compound

HRID 380034Notes

Reaction equation

HRID 380034 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C([N:8](CC)CC)C.[Br:13][C:14]1[CH:15]=[C:16]([S:20](Cl)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1>ClCCl>[N:1]1([NH:8][S:20]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([Br:13])[CH:15]=2)(=[O:22])=[O:21])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 17943m-Bromobenzenesulphonyl chlorideHCID 31268Pyrrolidine

Product 1

HCID 71436066HCID 71436066, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of pyrrolidine (0.33 ml) and triethylamine (0.6 ml) in dichloromethane (10 ml) was added dropwise to a stirred solution of 3-bromobenzenesulfonyl chloride (1 g) in dichloromethane (20 ml), and the mixture stirred at room temperature for 18 hours. The reaction was poured onto water, and the aqueous mixture was extracted with dichloromethane. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give an oil. This was purified by column chromatography over silica gel, eluting with ethyl acetate isohexane (1:4) to give the sub-title compound as a solid (1.10 g)

Workup

  1. additionThe reaction was poured onto water
  2. extractionthe aqueous mixture was extracted with dichloromethane
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give an oil
  8. customThis was purified by column chromatography over silica gel
  9. washeluting with ethyl acetate isohexane (1:4)

Sources & evidence

ORD record
ord-0a8edcf162324bd1bb3a327fd0cc526f
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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