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

HRID 635372Notes

Reaction equation

HRID 635372 reaction equation
[S:1]1[C:5]([C:6]2([C:10](=O)[CH2:11][Br:12])[CH2:9][CH2:8][CH2:7]2)=[CH:4][C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]1=2.[NH:18]1[CH2:22][CH2:21][NH:20][C:19]1=[S:23].C(O)C>C(O)(=O)C>[BrH:12].[S:1]1[C:5]([C:6]2([C:10]3[N:20]4[CH2:21][CH2:22][N:18]=[C:19]4[S:23][CH:11]=3)[CH2:9][CH2:8][CH2:7]2)=[CH:4][C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]1=2

Participants

5

Reactant 3

HCID 702EthanolHCID 2723650EthylenethioureaHCID 212585221-[1-(Benzo[b]thiophen-2-yl)cyclobutyl]-2-bromoethanone

Product 1

HCID 212584013-[1-(Benzo[b]thiophen-2-yl)cyclobutyl]-5,6-dihydroimidazo[2,1-b]thiazole hydrobromideYield 52.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-[1-(benzo[b]thiophen-2-yl)cyclobutyl]-2-bromoethanone (0.42 g), imidazolidine-2-thione (0.14 g), ethanol (15 ml) and acetic acid (10 ml) was heated under reflux for 18 hours then allowed to cool 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, dried in vacuo at 40° C. and crystallised from ethanol. The resulting product was collected by filtration, washed with ethanol (3 ml) and dried in vacuo at 40° C. to give 3-[1-(benzo[b]thiophen-2-yl)cyclobutyl]-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide as an off-white solid (0.28 g), m.p. 240-242° 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. customdried in vacuo at 40° C.
  7. customcrystallised from ethanol
  8. filtrationThe resulting product was collected by filtration
  9. washwashed with ethanol (3 ml)
  10. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-eec96c602eda4102991dd53be5d6e396
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

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