Hydrochloric Acid → HCID 67405889, compound

HRID 2205085Notes

Reaction equation

HRID 2205085 reaction equation
[CH3:1][C:2]1[S:6][C:5]2=[N:7][C:8]([CH2:10][C:11]([O:13]CC)=[O:12])=[CH:9][N:4]2[CH:3]=1.C(O)C.C(OCC)C.[ClH:24]>>[ClH:24].[CH3:1][C:2]1[S:6][C:5]2=[N:7][C:8]([CH2:10][C:11]([OH:13])=[O:12])=[CH:9][N:4]2[CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3283Diethyl EtherHCID 70817425Ethyl 2-(2-methylimidazo[2,1-b]thiazol-6-yl)acetate

Product 1

HCID 67405889HCID 67405889, compoundYield 93%

Procedure

Ethyl (2-methylimidazo[2,1-b][1,3]thiazol-6-yl)acetate (151.3 g, 0.67 mol) was dissolved in 10% aqueous HCl (435 mL) and the mixture was heated at reflux for 2 hours. The reaction mixture was cooled to room temperature and was concentrated in vacuo to give a yellow oil. Ethanol (100 mL) and diethylether (200 mL) were added and the resulting white precipitate was collected by filtration and dried in a vacuum oven overnight to give 144.3 g (93%) the title compound. MS (ES+) 197.1 (M+H)+. 1H NMR (CD3OD) δ 2.48 (s, 3H), 3.88 (s, 2H), 7.81 (s, 1H), 7.85 (s, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. concentrationwas concentrated in vacuo
  4. customto give a yellow oil
  5. filtrationthe resulting white precipitate was collected by filtration
  6. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-a94e8ebbdf8f4ed3aadebcaa739df1b9
Source dataset
uspto-grants-2016_06
Patent number
US09370516B2

Reaction notes

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