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

HRID 362260

Reaction equation

HRID 362260 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[O: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].[O: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 27765801-(Benzofuran-3-yl)-2-bromoethanone

Product 1

HCID 702844723-(Benzo[b]furan-3-yl)-5,6-dihydroimidazo[2,1-b]thiazole monohydrobromideYield 56.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-(2-bromoacetyl)benzo[b]furan (36.9 g), 2-imidazolidinethione (15.75 g), ethanol (600 ml) and acetic acid (400 ml) was heated under reflux for 21 hours then allowed to cool to ambient temperature. The resulting solid was collected by filtration, washed with ether (500 ml), and dissolved in hot methanol (500 ml). Charcoal (2 g) was added and the hot mixture was stirred for a few minutes, then filtered and allowed to cool to ambient temperature. The resulting solid was collected by filtration, ground to a fine powder, and dried in vacuo at 80° C. to give 3-(benzo[b]furan-3-yl)-5,6-dihydroimidazo[2,1-b]thiazole monohydrobromide 0.7 hydrate as an off-white solid (28.1 g), m.p. 251°-254.50C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 21 hours
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with ether (500 ml)
  5. dissolutiondissolved in hot methanol (500 ml)
  6. additionCharcoal (2 g) was added
  7. filtrationfiltered
  8. temperatureto cool to ambient temperature
  9. filtrationThe resulting solid was collected by filtration, ground to a fine powder
  10. customdried in vacuo at 80° C.

Sources & evidence

ORD record
ord-23c8818a734b430cb18040dd1fe1757f
Source dataset
uspto-grants-1999_02
Patent number
US05869492

Linked notes

Loading…