2-Aminothiazole → HCID 131728626, compound

HRID 1469967Notes

Reaction equation

HRID 1469967 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH2:7]([O:9][C:10](=[O:13])[CH2:11][Br:12])[CH3:8]>CC(C)=O>[BrH:12].[CH2:7]([O:9][C:10](=[O:13])[CH2:11][N:6]1[CH:5]=[CH:4][S:3][C:2]1=[NH:1])[CH3:8]

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 7748Ethyl bromoacetate

Product 1

HCID 131728626HCID 131728626, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-aminothiazole (27 g, 0.27 mol) and bromo-acetic acid ethyl ester (36 mL, 0.32 mol) in 540 mL of acetone was heated at 50° C. for 6 hours. The mixture was concentrated under reduced pressure and the residue was triturated with ethanol. The solid was collected by filtration to provide 58 g (80%) of the title compound. 1H NMR (DMSO-d6, 300 MHz) δ ppm 1.25 (t, J=7.1 Hz, 3H), 4.20 (q, J=7.1 Hz, 2H), 5.00 (s, 2H), 7.04 (d, J=4.7 Hz, 1H), 7.38 (d, J=4.7 Hz, 1H), 9.62 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was triturated with ethanol
  3. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-5ce1d072436a4b53b1ad229eff51ad8c
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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