2-Bromoethyl methyl ether → Ammonium Hydroxide

HRID 255136Notes

Reaction equation

HRID 255136 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][CH3:12]>>[NH4+:1].[OH-:11].[CH3:12][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 809722-Bromoethyl methyl etherHCID 3517702-Amino-5-methylthiazole

Product 2

HCID 14923Ammonium HydroxideHCID 668599523-(2-methoxyethyl)-5-methylthiazol-2(3H)-imine

Conditions

Temperature
85 °C

Procedure

A mixture of 2-amino-5-methylthiazole (10 g, 88 mmol) and 2-bromoethylmethyl ether (9.1 mL, 96 mmol) was warmed to 85° C. and stirred for 4.5 hours. The mixture was cooled to ambient temperature and the residue was purified via flash column chromatography (SiO2, 10% methanol in ethyl acetate then 9:1:0.1 CH2Cl2:methanol:NH4OH) to afford the title compound. MS (DCI/NH3) m/z 173 (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-7cc36994161d472892d64b0191a0b8be
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Reaction notes

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