Ethanol → HCID 21258397, compound

HRID 635358Notes

Reaction equation

HRID 635358 reaction equation
[Br:1][CH:2]([CH2:17][CH2:18][O:19][CH3:20])[C:3]([C:5]1([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)[CH2:8][CH2:7][CH2:6]1)=O.[NH:21]1[CH2:25][CH2:24][NH:23][C:22]1=[S:26].C(O)C>C(O)(=O)C>[BrH:1].[Cl:16][C:11]1[CH:10]=[C:9]([C:5]2([C:3]3[N:23]4[CH2:24][CH2:25][N:21]=[C:22]4[S:26][C:2]=3[CH2:17][CH2:18][O:19][CH3:20])[CH2:8][CH2:7][CH2:6]2)[CH:14]=[CH:13][C:12]=1[Cl:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723650EthylenethioureaHCID 21258374HCID 21258374, compound

Product 1

HCID 21258397HCID 21258397, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the crude 2-bromo-1-[1-(3,4-dichlorophenyl)cyclobutyl]-4-methoxybutan-1-one described above, imidazolidine-2-thione (0.68 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 vacua and the residue was dried by azeotropic distillation with ethanol (50 ml) followed by ethyl acetate (20 ml). The solid remaining after removal of residual solvent in vacuo was crystallised from a 2:1 mixture of ethanol and ethyl acetate. The resulting product was collected by filtration, washed with ethanol (10 ml) and dried in vacuo at 60°0 C. to give 3-[1-(3,4-dichlorophenyl)cyclobutyl]-2-(2-methoxyethyl)-5,6-dihydroimidazo[2,1-b]-thiazole hydrobromide as colourless prisms (1.39 g), m.p. 227-229° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customThe solvents were removed in vacua
  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 a 2:1 mixture of ethanol and ethyl acetate
  7. filtrationThe resulting product was collected by filtration
  8. washwashed with ethanol (10 ml)
  9. customdried in vacuo at 60°0 C

Sources & evidence

ORD record
ord-16fa286acdba4551bc6c6c3bff143706
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

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