2-Amino-4-methylthiazole → 3-(2-methoxyethyl)-4-methyl-1,3-thiazol-2(3H)-imine hydrobromide

HRID 78398

Reaction equation

HRID 78398 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1.[CH3:8][O:9][CH2:10][CH2:11][Br:12]>>[BrH:12].[CH3:8][O:9][CH2:10][CH2:11][N:3]1[C:2]([CH3:1])=[CH:6][S:5][C:4]1=[NH:7]

Participants

3

Reactant 2

HCID 741432-Amino-4-methylthiazoleHCID 809722-Bromoethyl methyl ether

Product 1

HCID 668596873-(2-methoxyethyl)-4-methyl-1,3-thiazol-2(3H)-imine hydrobromideYield 34%

Conditions

Temperature
85 °C

Procedure

A mixture of 4-methylthiazol-2-ylamine (0.75 g, 6.5 mmol) and 2-bromoethyl methyl ether (730 μL, 7.8 mmol) was heated at 85° C. for 15 hours. The mixture was cooled to ambient temperature and the resulting solid was triturated with isopropanol. Recrystallization from hot ethanol afforded 0.56 g (34%) of the title compound. 1H NMR (DMSO-d6, 300 MHz) δ ppm 2.25 (d, J=1.4 Hz, 3H) 3.25 (s, 3H) 3.57 (t, J=5.1 Hz, 2H) 4.15 (t, J=5.1 Hz, 2H) 6.68 (d, J=1.4 Hz, 1H) 9.40 (s, 1H); MS (DCI/NH3) m/z 173 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe resulting solid was triturated with isopropanol
  3. customRecrystallization from hot ethanol

Sources & evidence

ORD record
ord-16fa0f228d654dfbbf3ae26fb3ac0464
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

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