Sodium Octyl Sulfate → HCID 178443873, compound

HRID 45916Notes

Reaction equation

[Br-].[CH3:2][N:3]1[CH:7]=[CH:6][N+:5]([CH2:8][C:9]([O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][CH3:17])=[O:10])=[CH:4]1.[S:18]([O-:30])([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])(=[O:20])=[O:19].[Na+]>O>[CH2:22]([O:21][S:18]([O-:30])(=[O:20])=[O:19])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[CH3:2][N:3]1[CH:7]=[CH:6][N+:5]([CH2:8][C:9]([O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][CH3:17])=[O:10])=[CH:4]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-Methyl-1-(propoxyethoxycarbonylmethyl)imidazolium bromide (3.32 g, 12.0 mmol) in distilled water (20 mL) was added in one portion sodium octyl sulfate (2.09 g, 9.00 mmol) and stirred at 60° C. for 2 h. The water was then slowly removed under vacuum. The precipitate was dissolved in DCM (10 mL) and washed with distilled water (2×5 mL). The product remaining was dried on the rotary evaporator and then under high vacuum for 8 h to yield a dark yellow grease at RT in 85% yield (3.33 g, 7.64 mmol). 1H δ ppm 9.45 (s, 1H), 7.48 (t, J=1.6 Hz, 1H), 7.41 (t, J=1.6 Hz, 1H), 5.25 (5, 2H), 4.36 (t, J=4.8 Hz, 2H), 4.01 (s, 3H), 3.67 (t, J=4.6 Hz, 2H), 3.43 (t, J=6.8 Hz, 2H), 1.63-1.58 (m, 2H), 0.92-0.86 (m, 3H) 13C δ ppm 166.45, 138.89, 123.71, 123.06, 73.04, 67, 92, 67.89, 65.67, 49.91, 36.58, 31.83, 29.50, 29.36, 29.26, 25.87, 22.73, 22.66, 14.13, 10.47

Workup

customThe water was then slowly removed under vacuum
dissolutionThe precipitate was dissolved in DCM (10 mL)
washwashed with distilled water (2×5 mL)
customThe product remaining was dried on the rotary evaporator
customunder high vacuum for 8 h to yield a dark yellow grease at RT in 85% yield (3.33 g, 7.64 mmol)

Sources & evidence

ORD record: ord-858125896a6a4c1688ae71e9ac47c7cc
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541598B2

Reaction notes

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