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

HRID 635352Notes

Reaction equation

HRID 635352 reaction equation
[Br:1][CH2:2][C:3]([C:5]1([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)=O.[NH:18]1[CH2:22][CH2:21][NH:20][C:19]1=[S:23].C(O)C>C(O)(=O)C>[BrH:1].[Cl:17][C:12]1[CH:11]=[C:10]([C:5]2([C:3]3[N:20]4[CH2:21][CH2:22][N:18]=[C:19]4[S:23][CH:2]=3)[CH2:9][CH2:8][CH2:7][CH2:6]2)[CH:15]=[CH:14][C:13]=1[Cl:16]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723650EthylenethioureaHCID 212585122-Bromo-1-[1-(3,4-dichlorophenyl)cyclopentyl]ethanone

Product 1

HCID 212584093-[1-(3,4-Dichlorophenyl)cyclopentyl]-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-bromo-1-[1-(3,4-dichlorophenyl)cyclopentyl]ethanone (0.5 g), imidazolidine-2-thione (0.16 g), ethanol (3 ml) and acetic acid (2 ml) was heated under reflux for 18 hours then allowed to cool to ambient temperature. The solvents were removed in vacuo and the residue crystallised from a 1:1 mixture of ethyl acetate and ethanol. The resulting product was collected by filtration, washed with ethanol (3 ml) and dried in vacuo at 60° C. to give 3-[1-(3,4-dichlorophenyl)cyclopentyl]-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide as white microneedles (0.27 g), m.p. 230-232° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customThe solvents were removed in vacuo
  4. customthe residue crystallised from a 1:1 mixture of ethyl acetate and ethanol
  5. filtrationThe resulting product was collected by filtration
  6. washwashed with ethanol (3 ml)
  7. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-c910e2123d8c44a8b4fa76c3ac018f61
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

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