Butyl bromide → N'-(3-butyl-5-tert-butyl-1,3,4-thiadiazol-3-ium-2-yl)-N,N-dimethylmethanimidamide bromide

HRID 536769Notes

Reaction equation

[C:1]([C:5]1[S:9][C:8](/[N:10]=[CH:11]/[N:12]([CH3:14])[CH3:13])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:15][CH2:16][CH2:17][CH2:18][CH3:19]>C1(C)C=CC=CC=1>[Br-:15].[C:1]([C:5]1[S:9][C:8](/[N:10]=[CH:11]/[N:12]([CH3:14])[CH3:13])=[N+:7]([CH2:16][CH2:17][CH2:18][CH3:19])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of Example 162A (1.00 g, 4.71 mmol) in toluene (10 mL) was added 1-bromobutane (0.56 mL, 5.18 mmol). The mixture was heated at 100° C. for 12 hours, then cooled to ambient temperature and diluted with hexanes. The solid was collected by filtration (hexane wash) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.91 (t, J=7.5 Hz, 3H), 1.23-1.36 (m, 2H), 1.39 (s, 9H), 1.70-1.84 (m, 2H), 3.22 (s, 6H), 4.29 (t, J=7.1 Hz, 2H), 8.54 (s, 1H).

Workup

temperaturecooled to ambient temperature
filtrationThe solid was collected by filtration (hexane wash)

Sources & evidence

ORD record: ord-112da01829834b569e8c5cd23659d221
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859596B2

Reaction notes

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