Propane sultone → 1-propanaminium, n,n-dimethyl-n-(3-((2-methyl-1-oxo-2-propen-1-yl)amino)propyl)-3-sulfo-, inner salt

HRID 532071

Reaction equation

[CH2:1]1[S:5](=[O:7])(=[O:6])[O:4][CH2:3][CH2:2]1.[CH3:8][C:9]([C:11]([NH:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])=[O:12])=[CH2:10]>C(#N)C>[C:11]([NH:13][CH2:14][CH2:15][CH2:16][N+:17]([CH3:19])([CH3:18])[CH2:3][CH2:2][CH2:1][S:5]([O-:4])(=[O:7])=[O:6])(=[O:12])[C:9]([CH3:10])=[CH2:8]

Participants

Conditions

Temperature: 35 °C

Procedure

Into a round bottom flask is added 26.4 grams of anhydrous acetonitrile (available from Sigma-Aldrich) and 15.5 grams of propane sultone (available from Sigma-Aldrich), and this is stirred for 30 minutes. After the 30 minutes, a solution of 25.6 grams of DMAPMA in 56.5 grams of acetonitrile is added. The mixture is stirred and warmed to 35° C. A white precipitate quickly forms. Once the white precipitate takes up the bulk of the volume, the liquid is decanted. The solid is washed once with acetonitrile and again the liquid is removed by decanting. The solids are then washed in 2× volume diethyl ether. They are then filtered via funnel and washed with copious amounts (via filtration) of diethyl ether. The NMR structure is consistent with the structure of the target molecule SZ.

Workup

stirringThe mixture is stirred
customthe liquid is decanted
washThe solid is washed once with acetonitrile
customagain the liquid is removed
customby decanting
washThe solids are then washed in 2× volume diethyl ether
filtrationThey are then filtered via funnel
washwashed with copious amounts (via filtration) of diethyl ether

Sources & evidence

ORD record: ord-18fa32194ced452b8ae9a8e971c8a541
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08852399B2

Linked notes

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