Dimethylhexadecylamine → HCID 70390925, compound

HRID 1722626Notes

Reaction equation

[CH:1]([CH:3]([Cl:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:2].[CH2:11]([N:27]([CH3:29])[CH3:28])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>[Cl-:10].[CH:1]([CH2:2][CH:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:13][CH2:12][CH2:11][NH+:27]([CH3:29])[CH3:28])=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 50 °C

Procedure

In a 100 ml flask commercial vinylbenzyl chloride (3.05 g, 0.020 mol) was mixed with hexadecyldimethylamine (5.4 g, 0.020 mol) without any additional solvent. After addition of 2,6-di-tert-butyl-4-methylphenol (100 mg, 0.45 mmol) the mixture was heated overnight at 50° C. The solid product which formed was washed several times with dry ether, dried under vacuum at room temperature, and recrystallized from acetone/ether to give 6.3 g (75%) of 4-styrylmethyl (hexadecyl)dimethylammonium chloride. 1H NMR (CDCl3 /Me4Si): 0.88 (s, 3H), 1.24 (br s, 26H ), 1.78 (s, 2H), 3.30 (s, 6H), 3.53 (s, 2H), 5.08 (s, 2H), 5.32 (d, J=10.8 Hz, 1H), 5.84(d, J=18 Hz, 1H), 6.7 m, 1H), 7.51 (m, 4H). IR (KBr); 3020, 2920, 1640 cm-1. The critical micelle concentration (CMC) was 1.28× 10-2M at 25° C. determined conductometrically.

Workup

customThe solid product which formed
washwas washed several times with dry ether
customdried under vacuum at room temperature
customrecrystallized from acetone/ether

Sources & evidence

ORD record: ord-6b7c32855479448c82d25663395fb337
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04857493

Reaction notes

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