Methyl benzenesulfonate → HCID 22227621, compound

HRID 1744200Notes

Reaction equation

HRID 1744200 reaction equation
[CH2:1]([N:7]([CH2:14][C:15]#[N:16])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:17]1([S:23]([O:26]C)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(OCC)(=O)C>[C:17]1([S:23]([O-:26])(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:15]([CH2:14][N+:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH3:17])#[N:16]

Participants

4

Reactant 2

HCID 6630Methyl benzenesulfonateHCID 22227617HCID 22227617, compound

Product 1

HCID 22227621HCID 22227621, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

18.0 g (0.08 mol) of dihexylaminoacetonitrile were initially introduced into 50 ml of ethyl acetate. 13.8 g (0.08 mol) of methyl benzenesulfonate were added dropwise to this solution at room temperature over the course of 10 min. The mixture was stirred for 24 hours at room temperature, and the clear solution was concentrated by evaporation on a rotary evaporator. The residue was stirred out with diethyl ether and the precipitated solid was filtered off with suction. It was washed with diethyl ether and then dried at 50° C. in a vacuum drying cabinet. This gave 20.5 g (0.052 mol) of (cyanomethyl)-di-n-methylammonium benzenesulfonate of a white powder, corresponding to a yield of 65%.

Workup

  1. concentrationthe clear solution was concentrated by evaporation on a rotary evaporator
  2. stirringThe residue was stirred out with diethyl ether
  3. filtrationthe precipitated solid was filtered off with suction
  4. washIt was washed with diethyl ether
  5. customdried at 50° C. in a vacuum
  6. customdrying cabinet

Sources & evidence

ORD record
ord-4424dd8493984d508de40d1e819bd0b0
Source dataset
uspto-grants-2006_03
Patent number
US07015185B2

Reaction notes

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