Ethanol → HCID 21258509, compound

HRID 635350Notes

Reaction equation

HRID 635350 reaction equation
[Br:1][CH2:2][C:3]([C:5]1([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=2)[CH2:8][CH2:7][CH2:6]1)=O.[NH:19]1[CH2:23][CH2:22][NH:21][C:20]1=[S:24].C(O)C>C(O)(=O)C>[BrH:1].[CH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][C:9]=1[C:5]1([C:3]2[N:21]3[CH2:22][CH2:23][N:19]=[C:20]3[S:24][CH:2]=2)[CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 702EthanolHCID 2723650EthylenethioureaHCID 212584952-Bromo-1-[1-(2-naphthyl)cyclobutyl]ethanone

Product 1

HCID 21258509HCID 21258509, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the crude 2-bromo-1-[1-(2-naphthyl)cyclobutyl]ethanone described above, imidazolidine-2-thione (5.1 g), ethanol (60 ml) and acetic acid (40 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 a hot mixture of ethyl acetate (100 ml) and acetone (20 ml). The resulting solid was collected by filtration, washed with ethyl acetate (50 ml), dried in vacuo at 60° C., then crystallised from ethanol. The resulting solid was collected by filtration, washed with ethanol (30 ml), and dried in vacuo at 60° C. to give 3-[1-(2-naphthyl)cyclobutyl]-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide as pale yellow prisms (10 g), m.p. 239-241° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customThe solvents were removed in vacuo
  4. customthe residue was triturated with a hot mixture of ethyl acetate (100 ml) and acetone (20 ml)
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with ethyl acetate (50 ml)
  7. customdried in vacuo at 60° C.
  8. customcrystallised from ethanol
  9. filtrationThe resulting solid was collected by filtration
  10. washwashed with ethanol (30 ml)
  11. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-156e456459d84c7eb20ad2eda81b4488
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

Loading…