Ethanol → 3-(4-Chlorobenzo[b]thiophen-2-yl)-2-ethyl-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide

HRID 2183645Notes

Reaction equation

HRID 2183645 reaction equation
[Br:1][CH:2]([CH2:15][CH3:16])[C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][CH:12]=[C:13]([Cl:14])[C:7]=2[CH:6]=1)=O.[NH:17]1[CH2:21][CH2:20][NH:19][C:18]1=[S:22].C(O)C>C(O)(=O)C>[BrH:1].[Cl:14][C:13]1[C:7]2[CH:6]=[C:5]([C:3]3[N:19]4[CH2:20][CH2:21][N:17]=[C:18]4[S:22][C:2]=3[CH2:15][CH3:16])[S:9][C:8]=2[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 2723650EthylenethioureaHCID 224739972-Bromo-1-(4-chlorobenzo[b]thiophen-2-yl)butan-1-one

Product 1

HCID 224738223-(4-Chlorobenzo[b]thiophen-2-yl)-2-ethyl-5,6-dihydroimidazo[2,1-b]thiazole hydrobromideYield 71.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-bromo-1-(4-chlorobenzo[b]thiophen-2-yl)butan-1-one (1.06 g), 2-imidazolidinethione (0.255 g) and ethanol (25 ml) was heated under reflux for 20 minutes. Acetic acid (12 ml) was added, the mixture was heated under reflux for 21 hours, then the solvents were removed in vacuo and the solid residue recrystallised from propan-2-ol (40 ml) to give 3-(4-chlorobenzo[b]thiophen-2-yl)-2-ethyl-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide (0.72 g) as a white solid, m.p. 187-189° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 minutes
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 21 hours
  5. customthe solvents were removed in vacuo
  6. customthe solid residue recrystallised from propan-2-ol (40 ml)

Sources & evidence

ORD record
ord-67c19d293d4f43d8bafa21e1ac13f0dd
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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