Ethanol → 3-(Benzo[b]thiophen-4-yl)-5,6-dihydroimidazo[2,1-b]thiazole hydrochloride

HRID 2183592

Reaction equation

HRID 2183592 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([C:10](=O)[CH2:11][Cl:12])=[CH:7][CH:8]=[CH:9][C:2]1=2.[NH:14]1[CH2:18][CH2:17][NH:16][C:15]1=[S:19].C(O)C>C(O)(=O)C>[ClH:12].[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([C:10]3[N:16]4[CH2:17][CH2:18][N:14]=[C:15]4[S:19][CH:11]=3)=[CH:7][CH:8]=[CH:9][C:2]1=2

Participants

5

Reactant 3

HCID 702EthanolHCID 2723650EthylenethioureaHCID 224737991-(Benzo[b]thiophen-4-yl)-2-chloroethan-1-one

Product 1

HCID 224738373-(Benzo[b]thiophen-4-yl)-5,6-dihydroimidazo[2,1-b]thiazole hydrochlorideYield 107.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(benzo[b]thiophen-4-yl)-2-chloroethan-1-one (1.15 g), 2-imidazolidinethione (0.57 g), ethanol (10 ml) and acetic acid (6 ml) was heated under reflux for 18 hours then cooled to ambient temperature. The solvents were removed in vacuo and the residue was triturated with ether (30 ml). The resulting solid was collected by filtration, washed with ether (30 ml) and dried in vacuo at 40° C. to give 3-(benzo[b]thiophen-4-yl)-5,6-dihydroimidazo[2,1-b]thiazole hydrochloride (1.73 g) as a cream solid, m.p. 246-249° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customThe solvents were removed in vacuo
  4. customthe residue was triturated with ether (30 ml)
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with ether (30 ml)
  7. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-5817eaaee1a84fc79c01a652dd385234
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Linked notes

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