2-Aminothiazole → HCID 66860916, compound

HRID 78396Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH3:7][O:8][CH2:9][CH2:10][Br:11]>>[BrH:11].[CH3:7][O:8][CH2:9][CH2:10][N:6]1[CH:5]=[CH:4][S:3][C:2]1=[NH:1]

Participants

Reactant 2

HCID 21552-Aminothiazole

HCID 809722-Bromoethyl methyl ether

Product 1

HCID 66860916HCID 66860916, compoundYield 72.5%

Conditions

Temperature: 85 °C

Procedure

A mixture of 2-aminothiazole (15 g, 0.15 mol) and 2-bromoethyl methyl ether (17 mL, 0.18 mol) were heated at 85° C. for 16 hours. After cooling to ambient temperature the resulting solid was triturated twice with isopropyl alcohol to afford 26 g (72%) of the title compound. 1H NMR (DMSO-d6, 300 MHz) δ ppm 3.27 (s, 3H), 3.63 (t, J=5.1 Hz, 2H), 4.23 (t, J=4.9 Hz, 2H), 7.02 (d, J=4.7 Hz, 1H), 7.38 (d, J=4.4 Hz, 1H), 9.52 (s, 1H); MS (DCI/NH3) m/z 159 (M+H)+.

Workup

temperatureAfter cooling to ambient temperature the resulting solid
customwas triturated twice with isopropyl alcohol

Sources & evidence

ORD record: ord-9822afeace7a449cb1364150c24766ba
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841334B2

Reaction notes

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