2-Bromoethyl methyl ether → 3-(2-Methoxyethyl)-5-methyl-3H-thiazol-2-ylideneamine hydrobromide

HRID 78402

Reaction equation

HRID 78402 reaction equation
[CH3:1][C:2]1[S:6][C:5]([NH2:7])=[N:4][CH:3]=1.[CH3:8][O:9][CH2:10][CH2:11][Br:12]>>[BrH:12].[CH3:8][O:9][CH2:10][CH2:11][N:4]1[CH:3]=[C:2]([CH3:1])[S:6][C:5]1=[NH:7]

Participants

3

Reactant 2

HCID 809722-Bromoethyl methyl etherHCID 3517702-Amino-5-methylthiazole

Product 1

HCID 668601993-(2-Methoxyethyl)-5-methyl-3H-thiazol-2-ylideneamine hydrobromideYield 40.4%

Conditions

Temperature
85 °C

Procedure

A mixture of 5-methyl-thiazol-2-ylamine (1.0 g, 8.8 mmol) and 2-bromoethyl methyl ether (1.0 mL, 11 mmol) were heated at 85° C. for 16 hours. The mixture was cooled to ambient temperature, triturated with ethanol and the solid was collected by filtration to afford 0.90 g (40%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ ppm 2.25 (d, J=1.4 Hz, 3H), 3.36 (s, 3H), 3.72-3.81 (m, 2H), 4.36-4.43 (m, 2H), 6.61 (d, J=1.7 Hz, 1H), 9.54 (s, 1H); MS (DCI/NH3) m/z 173 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customtriturated with ethanol
  3. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-ab8a3ea2a1984611bdc7f72493eab221
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

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