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

HRID 362253

Reaction equation

HRID 362253 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:4].[NH:14]1[CH2:18][CH2:17][NH:16][C:15]1=[S:19].C([OH:22])C>C(O)(=O)C>[OH2:4].[OH2:22].[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 687790213-(Benzo[b]thiophen-3-yl)-5,6-dihydroimidazo[2,1-b]thiazole monohydrobromide dihydrate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-(2-bromoacetyl)benzo[b]thiophen (2.39 g), 2-imidazolidinethione (0.78 g), ethanol (60 ml) and acetic acid (40 ml) was heated under reflux for 18 hours then allowed to cool to ambient temperature. The resulting solid was collected by filtration, washed with ether (2×50 ml), and dried in vacuo at ambient temperature to give 3-(benzo[b]thiophen-3-yl)-5,6-dihydroimidazo[2,1 -b]thiazole monohydrobromide dihydrate as a white solid (2.96 g), m.p. 239°-240° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with ether (2×50 ml)
  5. customdried in vacuo at ambient temperature

Sources & evidence

ORD record
ord-fd09965459ef41efa16387e585faa295
Source dataset
uspto-grants-1999_02
Patent number
US05869492

Linked notes

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