Ethanol → HCID 22474170, compound

HRID 2183632Notes

Reaction equation

HRID 2183632 reaction equation
[S:1]1[C:5]([C:6](=O)[CH2:7][Br:8])=[CH:4][C:3]2[CH:10]=[CH:11][CH:12]=[CH:13][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>[BrH:8].[S:1]1[C:5]([C:6]2[N:16]3[CH2:17][CH2:18][N:14]=[C:15]3[S:19][CH:7]=2)=[CH:4][C:3]2[CH:10]=[CH:11][CH:12]=[CH:13][C:2]1=2

Participants

5

Reactant 3

HCID 702EthanolHCID 2723650EthylenethioureaHCID 27952581-(1-Benzothiophen-2-yl)-2-bromoethan-1-one

Product 1

HCID 22474170HCID 22474170, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(benzo[b]thiophen-2-yl)-2-bromoethan-1-one (21.96 g), 2-imidazolidinethione (7.81 g) and ethanol (300 ml) was heated under reflux for 10 minutes. Acetic acid (150 ml) was added, then the mixture was heated under reflux for 18 hours and allowed to cool to ambient temperature. The resulting solid was collected by filtration, washed with ethanol (50 ml) and ether (50 ml), then dried in vacuo at 100° C. for 3 hours to give 3-(benzo[b]thiophen-2-yl)-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide (19.6 g) as a light brown solid, m.p. 275-285° C. (decomposes).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 minutes
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 18 hours
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with ethanol (50 ml) and ether (50 ml)
  7. customdried in vacuo at 100° C. for 3 hours

Sources & evidence

ORD record
ord-3b12617c00734856bfe4e0e0734ef99f
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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