Ethanol → 2-(4-Chlorophenyl)-3-[1-(3,4-dichlorophenyl)cyclobutyl]-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide

HRID 635364Notes

Reaction equation

HRID 635364 reaction equation
[Br:1][CH:2]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[C:3]([C:5]1([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)[CH2:8][CH2:7][CH2:6]1)=O.[NH:24]1[CH2:28][CH2:27][NH:26][C:25]1=[S:29].C(O)C>C(O)(=O)C>[BrH:1].[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([C:2]2[S:29][C:25]3=[N:24][CH2:28][CH2:27][N:26]3[C:3]=2[C:5]2([C:9]3[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=3)[CH2:8][CH2:7][CH2:6]2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 2723650EthylenethioureaHCID 212583922-Bromo-2-(4-chlorophenyl)1-[1-(3,4-dichlorophenyl)cyclobutyl]ethanone

Product 1

HCID 212584932-(4-Chlorophenyl)-3-[1-(3,4-dichlorophenyl)cyclobutyl]-5,6-dihydroimidazo[2,1-b]thiazole hydrobromideYield 21.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-bromo-2-(4-chlorophenyl)1-[1-(3,4-dichlorophenyl)cyclobutyl]ethanone (3.68 g), imidazolidine-2-thione (0.87 g), ethanol (60 ml) and acetic acid (35 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 ethanol (30 ml). The resulting solid was collected by filtration and crystallised from acetic acid. The resulting product was collected by filtration, washed with acetic acid (10 ml) and dried in vacuo at 100° C. to give 2-(4-chlorophenyl)-3-[1-(3,4-dichlorophenyl)cyclobutyl]-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide as a colourless solid (0.93 g), m.p. 302-304° C. (decomposes).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customThe solvents were removed in vacuo
  4. customthe residue was triturated with ethanol (30 ml)
  5. filtrationThe resulting solid was collected by filtration
  6. customcrystallised from acetic acid
  7. filtrationThe resulting product was collected by filtration
  8. washwashed with acetic acid (10 ml)
  9. customdried in vacuo at 100° C.

Sources & evidence

ORD record
ord-15557f8a0bac45938342ef6fdde98d1f
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

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