Ethanol → 3-[1-(3,4-Dichlorophenyl)-1-methylethyl]-5,6-dihydroimidazo[2,1-b]-thiazole hydrobromide

HRID 635367Notes

Reaction equation

HRID 635367 reaction equation
[Br:1][CH2:2][C:3](=O)[C:4]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)([CH3:6])[CH3:5].[NH:16]1[CH2:20][CH2:19][NH:18][C:17]1=[S:21].C(O)C>C(O)(=O)C>[BrH:1].[Cl:14][C:9]1[CH:8]=[C:7]([C:4]([C:3]2[N:18]3[CH2:19][CH2:20][N:16]=[C:17]3[S:21][CH:2]=2)([CH3:6])[CH3:5])[CH:12]=[CH:11][C:10]=1[Cl:13]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723650EthylenethioureaHCID 212583981-Bromo-3-(3,4-dichlorophenyl)-3-methylbutan-2-one

Product 1

HCID 212584713-[1-(3,4-Dichlorophenyl)-1-methylethyl]-5,6-dihydroimidazo[2,1-b]-thiazole hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the crude 1-bromo-3-(3,4-dichlorophenyl)-3-methylbutan-2-one described above (3.1 g), imidazolidine-2-thione (1.2 g), ethanol (1.02 ml) and acetic acid (8 ml) was heated under reflux for 22 hours then allowed to cool to ambient temperature. The solvents were removed in vacuo and the residue was triturated with hot ethyl acetate (80 ml). The resulting solid was collected by filtration, washed with ethyl acetate (20 ml), dried in vacuo at 50° C., then crystallised from ethanol. The resulting product was collected by filtration, washed with ethanol (5 ml) and dried in vacuo at 50° C. to give 3-[1-(3,4-dichlorophenyl)-1-methylethyl]-5,6-dihydroimidazo[2,1-b]-thiazole hydrobromide as an off-white solid (0.95 g), m.p. 266-270° C. (decomposes).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 22 hours
  3. customThe solvents were removed in vacuo
  4. customthe residue was triturated with hot ethyl acetate (80 ml)
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with ethyl acetate (20 ml)
  7. customdried in vacuo at 50° C.
  8. customcrystallised from ethanol
  9. filtrationThe resulting product was collected by filtration
  10. washwashed with ethanol (5 ml)
  11. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-9966912d0ed44dce9b1e1b7922705087
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

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