1-Bromo-3,6-dioxaheptane → Ammonium Hydroxide

HRID 255120

Reaction equation

HRID 255120 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:7])=[CH:5][N:6]=1.Br[CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15]>>[NH4+:1].[OH-:11].[CH3:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][N:6]1[CH:5]=[C:4]([CH3:7])[S:3][C:2]1=[NH:1]

Participants

4

Reactant 2

HCID 1235321-Bromo-3,6-dioxaheptaneHCID 3517702-Amino-5-methylthiazole

Product 2

HCID 14923Ammonium HydroxideHCID 668587283-(2-(2-methoxyethoxy)ethyl)-5-methylthiazol-2(3H)-imine

Conditions

Temperature
85 °C

Procedure

A mixture of 2-amino-5-methylthiazole (1.5 g, 13.0 mmol) and 1-bromo-2-(2-methoxyethoxy)ethane (2.0 mL, 14.5 mmol) was warmed to 85° C. and stirred for 5 hours. The mixture was cooled to ambient temperature and the residue was purified via flash column chromatography (SiO2, 10% methanol in ethyl acetate then 9:1:01 CH2Cl2:methanol:NH4OH) to afford the title compound. MS (DCI/NH3) m/z 217 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-b76b92c8e42c49d5a61c8cd2d148337e
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Linked notes

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