Ethanol → HCID 21258516, compound

HRID 635355Notes

Reaction equation

HRID 635355 reaction equation
[Br:1][CH:2]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:3]([C:5]1([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6]1)=O.[NH:23]1[CH2:27][CH2:26][NH:25][C:24]1=[S:28].C(O)C>C(O)(=O)C>[BrH:1].[CH2:16]([C:2]1[S:28][C:24]2=[N:23][CH2:27][CH2:26][N:25]2[C:3]=1[C:5]1([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 2723650EthylenethioureaHCID 21258466HCID 21258466, compound

Product 1

HCID 21258516HCID 21258516, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the crude 2-bromo-1-[1-(4-chlorophenyl)cyclobutyl]-3-phenylpropan-1-one described above, imidazolidine-2-thione (1.02 g), ethanol (15 ml) and acetic acid (10 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 dried by azeotropic distillation with ethanol (50 ml) followed by ethyl acetate (50 ml). The solid remaining after removal of residual solvent in vacuo was crystallised from ethanol. The resulting product was collected by filtration, washed with ethanol (10 ml) and dried in vacuo at 60° C. to give 2-benzyl-3-[1-(4-chlorophenyl)cyclobutyl]-5,6-dihydroimidazo[2,1-b]-thiazole hydrobromide as white microneedles (2 g), m.p. 255-257° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customThe solvents were removed in vacuo
  4. dry with materialthe residue was dried by azeotropic distillation with ethanol (50 ml)
  5. customafter removal of residual solvent in vacuo
  6. customwas crystallised from ethanol
  7. filtrationThe resulting product was collected by filtration
  8. washwashed with ethanol (10 ml)
  9. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-db118e09af9f4a7da8b935c919aed534
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

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