Methyl iodide → 2-(1-Pyrrolidinylmethyl)benzenesulfonamide, methyl iodide salt

HRID 4144Notes

Reaction equation

HRID 4144 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:13]([NH2:16])(=[O:15])=[O:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:17][I:18]>C(#N)C>[I-:18].[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:13]([NH:16][CH3:17])(=[O:14])=[O:15])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 133646292-(Pyrrolidin-1-ylmethyl)benzenesulfonamide

Product 1

HCID 1317139882-(1-Pyrrolidinylmethyl)benzenesulfonamide, methyl iodide salt

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-(pyrrolidinomethyl)benzenesulfonamide (0.8 g) in acetonitrile (10 ml) was contacted with methyl iodide (3 ml) and heated to reflux for 2.0 hrs. Solvent was removed and the residue was treated with acetone and ether. The solid was filtered, digested with acetone (20 ml), chilled and collected. There was obtained 1.00 g of white solid. 1H nmr δDMSO-d6TMS 8.15-7.30 (m), 5.07 (s, 2H), 3.9-3.3 (m, 4H), 2.90 (s, 3H), 2.4-1.8 (m, 4H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2.0 hrs
  3. customSolvent was removed
  4. additionthe residue was treated with acetone and ether
  5. filtrationThe solid was filtered
  6. temperaturechilled
  7. customcollected

Sources & evidence

ORD record
ord-a1d6ecf5affe4cdc9339c195051b4e6a
Source dataset
uspto-grants-1988_02
Patent number
US04723990

Reaction notes

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