2-Bromoethyl methyl ether → Ammonia

HRID 255116Notes

Reaction equation

HRID 255116 reaction equation
[C:1]([C:5]1[S:9][C:8]([NH2:10])=[N:7][C:6]=1[CH3:11])([CH3:4])([CH3:3])[CH3:2].[CH3:12][O:13][CH2:14][CH2:15]Br>>[NH4+:7].[OH-:13].[C:1]([C:5]1[S:9][C:8](=[NH:10])[N:7]([CH2:15][CH2:14][O:13][CH3:12])[C:6]=1[CH3:11])([CH3:4])([CH3:3])[CH3:2].[NH3:7]

Participants

5

Reactant 2

HCID 809722-Bromoethyl methyl etherHCID 10815365-tert-Butyl-4-methyl-thiazol-2-ylamine

Product 3

HCID 222AmmoniaHCID 14923Ammonium HydroxideHCID 66858523HCID 66858523, compound

Conditions

Temperature
85 °C

Procedure

A mixture of 5-tert-butyl-4-methylthiazole-2-ylamine (Matrix, 1.5 g, 8.8 mmol) and 2-bromoethyl methyl ether (0.91 mL, 9.7 mmol) was warmed to 85° C. and allowed to stir for 24 hours. The mixture was cooled to ambient temperature and material 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 229 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-e1c1dc948168451484c0d5ce20ed717b
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Reaction notes

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