Benzene, (2-bromoethoxy)- → 4,5-Dimethyl-3-(2-phenoxy-ethyl)-3H-thiazol-2-ylideneamine hydrobromide

HRID 78406

Reaction equation

HRID 78406 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:8])[S:5][C:6]=1[CH3:7].[Br:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[BrH:9].[CH3:1][C:2]1[N:3]([CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4](=[NH:8])[S:5][C:6]=1[CH3:7]

Participants

3

Reactant 2

HCID 68526Benzene, (2-bromoethoxy)-HCID 732382-Amino-4,5-dimethyl-1,3-thiazole

Product 1

HCID 686212084,5-Dimethyl-3-(2-phenoxy-ethyl)-3H-thiazol-2-ylideneamine hydrobromideYield 50.6%

Conditions

Temperature
85 °C

Procedure

A mixture of 4,5-dimethylthiazol-2-ylamine (1.0 g, 7.8 mmol) and (2-bromo-ethoxy)benzene (1.9 g, 9.4 mmol) were heated neat to 85° C. for 19 hours. The mixture was cooled to ambient temperature and the residue was crystallized from isopropanol. The solid was collected by filtration and dried under vacuum to afford 1.3 g (50%) of the title compound. MS (DCI/NH3) m/z 249 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe residue was crystallized from isopropanol
  3. filtrationThe solid was collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-83cb530fe84542689d937de7db6523a9
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

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