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

HRID 362255

Reaction equation

HRID 362255 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[S:8][CH:9]=1)=O.[NH:14]1[CH2:18][CH2:17][NH:16][C:15]1=[S:19].C(O)C>C(O)(=O)C>[BrH:1].[S:8]1[CH:9]=[C:5]([C:3]2[N:16]3[CH2:17][CH2:18][N:14]=[C:15]3[S:19][CH:2]=2)[C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]1=2

Participants

5

Reactant 3

HCID 702EthanolHCID 2723650EthylenethioureaHCID 27763411-(1-Benzothiophen-3-yl)-2-bromoethan-1-one

Product 1

HCID 510719843-(Benzo[b]thiophen-3-yl)-5,6-dihydroimidazo[2,1-b]thiazole monohydrobromideYield 87.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-(2-bromoacetyl)benzo[b]thiophen (10.0 g), 2-imidazolidinethione (4.0 g), ethanol (120 ml) and acetic acid (80 ml) was heated under reflux for 24 hours then allowed to cool to ambient temperature. The resulting solid was collected by filtration and dried in vacuo at ambient temperature to give 3-(benzo[b]thiophen-3-yl)-5,6-dihydroimidazo[2,1-b]thiazole monohydrobromide 1.8 hydrate as a white solid (11.6 g), m.p. 227°-229° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. filtrationThe resulting solid was collected by filtration
  4. customdried in vacuo at ambient temperature

Sources & evidence

ORD record
ord-4f580d759c6347298f2ae97b8ee1ba13
Source dataset
uspto-grants-1999_02
Patent number
US05869492

Linked notes

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