1-[1-(3,4-Dichlorophenyl)cyclobutyl]-2-(2-imidazolin-2-ylthio)ethanone hydrobromide → 3-[1-(3,4-Dichlorophenyl)cyclobuty]-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide

HRID 635339Notes

Reaction equation

HRID 635339 reaction equation
[BrH:1].[Cl:2][C:3]1[CH:4]=[C:5]([C:10]2([C:14](=O)[CH2:15][S:16][C:17]3[NH:18][CH2:19][CH2:20][N:21]=3)[CH2:13][CH2:12][CH2:11]2)[CH:6]=[CH:7][C:8]=1[Cl:9]>C(O)(=O)C>[BrH:1].[Cl:2][C:3]1[CH:4]=[C:5]([C:10]2([C:14]3[N:21]4[CH2:20][CH2:19][N:18]=[C:17]4[S:16][CH:15]=3)[CH2:13][CH2:12][CH2:11]2)[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

3

Reactant 1

HCID 212585071-[1-(3,4-Dichlorophenyl)cyclobutyl]-2-(2-imidazolin-2-ylthio)ethanone hydrobromide

Product 1

HCID 701076903-[1-(3,4-Dichlorophenyl)cyclobuty]-5,6-dihydroimidazo[2,1-b]thiazole hydrobromideYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred suspension of 1-[1-(3,4-dichlorophenyl)cyclobutyl]-2-(2-imidazolin-2-ylthio)ethanone hydrobromide (5 g) in acetic acid (20 ml) was heated under reflux for 18 hours then allowed to cool to ambient temperature. The solvent was removed in vacuo, the residue was allowed to stand at ambient temperature for 24 hours, and the resulting solid was triturated with ether (50 ml), collected by filtration, washed with ether (50 ml) and dried in vacuo at 50° C. for 3 hours to give 3-[1-(3,4-dichlorophenyl)cyclobuty]-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide as a white solid (4.5 g), m.p. 241-244° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customThe solvent was removed in vacuo
  4. customthe resulting solid was triturated with ether (50 ml)
  5. filtrationcollected by filtration
  6. washwashed with ether (50 ml)
  7. customdried in vacuo at 50° C. for 3 hours

Sources & evidence

ORD record
ord-2265150fff3e4812a6887c87630b65ec
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

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