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

HRID 2183620Notes

Reaction equation

HRID 2183620 reaction equation
[Br:1][CH:2]([CH2:15][CH3:16])[C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][C:12]([Cl:14])=[CH:13][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:12]1[CH:11]=[CH:10][C:8]2[S:9][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])=[CH:6][C:7]=2[CH:13]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 2723650EthylenethioureaHCID 224740212-Bromo-1-(5-chlorobenzo[b]thiophen-2-yl)butan-1-one

Product 1

HCID 224739283-(5-Chlorobenzo[b]thiophen-2-yl)-2-ethyl-5,6-dihydroimidazo[2,1-b]thiazole hydrobromideYield 63.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-bromo-1-(5-chlorobenzo[b]thiophen-2-yl)butan-1-one (1 g), 2-imidazolidinethione (0.32 g), ethanol (30 ml) and acetic acid (15 ml) was heated under reflux for 24 hours, then the solvents were removed in vacuo. The residue was crystallised from ethanol (100 ml) and the resulting solid was collected by filtration, washed with ethanol (10 ml) and dried in vacuo at 60° C. to give 3-(5-chlorobenzo[b]thiophen-2-yl)-2-ethyl-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide (0.8 g) as a white solid, m.p. 282-284° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. customthe solvents were removed in vacuo
  4. customThe residue was crystallised from ethanol (100 ml)
  5. filtrationthe resulting solid was collected by filtration
  6. washwashed with ethanol (10 ml)
  7. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-8ff4622e8a9e41ae8468e1744d06b0dd
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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