Furan, 2-(bromomethyl)tetrahydro- → Ammonium Hydroxide

HRID 78465

Reaction equation

HRID 78465 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:7])=[CH:5][N:6]=1.Br[CH2:9][CH:10]1[CH2:14][CH2:13][CH2:12][O:11]1>>[NH4+:1].[OH-:11].[CH3:7][C:4]1[S:3][C:2](=[NH:1])[N:6]([CH2:9][CH:10]2[CH2:14][CH2:13][CH2:12][O:11]2)[CH:5]=1

Participants

4

Reactant 2

HCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 3517702-Amino-5-methylthiazole

Product 2

HCID 14923Ammonium HydroxideHCID 668516985-methyl-3-((tetrahydrofuran-2-yl)methyl)thiazol-2(3H)-imine

Conditions

Temperature
85 °C

Procedure

A mixture of 2-amino-5-methylthiazole (1 g, 8.7 mmol) and 2-(bromomethyl)tetrahydrofuran (1.1 mL, 10 mmol) was warmed to 85° C. and was allowed to stir for 24 hours. The mixture was cooled to ambient temperature and purified via flash 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. custompurified via flash column chromatography (SiO2, 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-29a97a4affdc422abe28ffd2721749b1
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

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