Ethyl bromoacetate → HCID 66858960, compound

HRID 255109Notes

Reaction equation

HRID 255109 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH2:10].[CH2:11]([O:13][C:14](=[O:17])[CH2:15][Br:16])[CH3:12]>CC(C)=O>[BrH:16].[CH2:11]([O:13][C:14](=[O:17])[CH2:15][N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][C:2]1=[NH:10])[CH3:12]

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 8706Benzo(d)thiazol-2-amine

Product 1

HCID 66858960HCID 66858960, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of benzothiazol-2-ylamine (1.0 g, 6.6 mmol) and bromoacetic acid ethyl ester (0.86 mL, 7.9 mmol) in 30 mL of acetone was heated at 50° C. for 6 hours. The mixture was cooled to ambient temperature and the solid was triturated with ethanol, collected by filtration, and dried under vacuum to provide 1.8 g (86%) of the title compound. 1H NMR (DMSO-d6, 300 MHz) δ ppm 1.25 (t, J=7.1 Hz, 3 H), 4.22 (q, J=7.1 Hz, 2 H), 5.28 (s, 2 H), 7.44 (td, J=7.6, 1.0 Hz, 1 H), 7.55 (td, J=7.8, 1.4 Hz, 1 H), 7.68 (d, J=7.8 Hz, 1 H), 8.01 (dd, J=8.1, 1.0 Hz, 1 H), 10 3 (s, 1H); MS (DCI/NH3) m/z 237 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe solid was triturated with ethanol
  3. filtrationcollected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-772e1048f7124b6296550e7f913c9ba5
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Reaction notes

Loading…