2-Aminothiazole → Ammonium Hydroxide

HRID 78469Notes

Reaction equation

HRID 78469 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.Br[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1>>[NH4+:1].[OH-:10].[O:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]1[CH2:8][N:6]1[CH:5]=[CH:4][S:3][C:2]1=[NH:1]

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 1419172-(Bromomethyl)tetrahydro-2H-pyran

Product 2

HCID 14923Ammonium HydroxideHCID 686230663-((tetrahydro-2H-pyran-2-yl)methyl)thiazol-2(3H)-imine

Conditions

Temperature
85 °C

Procedure

A mixture of 2-aminothiazole (1.0 g, 10 mmol) and 2-(bromomethyl)tetrahydro-2H-pyran (1.3 mL, 10 mmol) was warmed to 85° C. and was allowed to stir for 24 hours. The mixture was cooled to ambient temperature and the crude material was purified via column chromatography (SiO2, 10% methanol in ethyl acetate then 9:1:0.1 CH2Cl2:methanol:NH4OH) to afford the title compound. MS (DCI/NH3) m/z 199 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe crude material was purified via column chromatography (SiO2, 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-9c341b032d00464bbb11e05c4adbcd36
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Reaction notes

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